EP3458446A1 - Dérivés d'oxadiazole microbiocides - Google Patents

Dérivés d'oxadiazole microbiocides

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Publication number
EP3458446A1
EP3458446A1 EP17726886.9A EP17726886A EP3458446A1 EP 3458446 A1 EP3458446 A1 EP 3458446A1 EP 17726886 A EP17726886 A EP 17726886A EP 3458446 A1 EP3458446 A1 EP 3458446A1
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EP
European Patent Office
Prior art keywords
alkyl
hydrogen
phenyl
methyl
formula
Prior art date
Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
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Application number
EP17726886.9A
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German (de)
English (en)
Inventor
Thomas James HOFFMAN
Daniel Stierli
Farhan BOU HAMDAN
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Syngenta Participations AG
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Syngenta Participations AG
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Publication of EP3458446A1 publication Critical patent/EP3458446A1/fr
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Classifications

    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D271/00—Heterocyclic compounds containing five-membered rings having two nitrogen atoms and one oxygen atom as the only ring hetero atoms
    • C07D271/02—Heterocyclic compounds containing five-membered rings having two nitrogen atoms and one oxygen atom as the only ring hetero atoms not condensed with other rings
    • C07D271/06—1,2,4-Oxadiazoles; Hydrogenated 1,2,4-oxadiazoles
    • A—HUMAN NECESSITIES
    • A01—AGRICULTURE; FORESTRY; ANIMAL HUSBANDRY; HUNTING; TRAPPING; FISHING
    • A01N—PRESERVATION OF BODIES OF HUMANS OR ANIMALS OR PLANTS OR PARTS THEREOF; BIOCIDES, e.g. AS DISINFECTANTS, AS PESTICIDES OR AS HERBICIDES; PEST REPELLANTS OR ATTRACTANTS; PLANT GROWTH REGULATORS
    • A01N43/00—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds
    • A01N43/72—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with nitrogen atoms and oxygen or sulfur atoms as ring hetero atoms
    • A01N43/82—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with nitrogen atoms and oxygen or sulfur atoms as ring hetero atoms five-membered rings with three ring hetero atoms
    • A—HUMAN NECESSITIES
    • A01—AGRICULTURE; FORESTRY; ANIMAL HUSBANDRY; HUNTING; TRAPPING; FISHING
    • A01N—PRESERVATION OF BODIES OF HUMANS OR ANIMALS OR PLANTS OR PARTS THEREOF; BIOCIDES, e.g. AS DISINFECTANTS, AS PESTICIDES OR AS HERBICIDES; PEST REPELLANTS OR ATTRACTANTS; PLANT GROWTH REGULATORS
    • A01N43/00—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds
    • A01N43/90—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having two or more relevant hetero rings, condensed among themselves or with a common carbocyclic ring system
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D271/00—Heterocyclic compounds containing five-membered rings having two nitrogen atoms and one oxygen atom as the only ring hetero atoms
    • C07D271/02—Heterocyclic compounds containing five-membered rings having two nitrogen atoms and one oxygen atom as the only ring hetero atoms not condensed with other rings
    • C07D271/10—1,3,4-Oxadiazoles; Hydrogenated 1,3,4-oxadiazoles
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D413/00—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and oxygen atoms as the only ring hetero atoms
    • C07D413/02—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and oxygen atoms as the only ring hetero atoms containing two hetero rings
    • C07D413/12—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and oxygen atoms as the only ring hetero atoms containing two hetero rings linked by a chain containing hetero atoms as chain links
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D498/00—Heterocyclic compounds containing in the condensed system at least one hetero ring having nitrogen and oxygen atoms as the only ring hetero atoms
    • C07D498/02—Heterocyclic compounds containing in the condensed system at least one hetero ring having nitrogen and oxygen atoms as the only ring hetero atoms in which the condensed system contains two hetero rings
    • C07D498/08—Bridged systems

Definitions

  • the present invention relates to microbiocidal oxadiazole derivatives, e.g., as active ingredients, which have microbiocidal activity, in particular, fungicidal activity.
  • the invention also relates to agrochemical compositions which comprise at least one of the oxadiazole derivatives, to processes of preparation of these compounds and to uses of the oxadiazole derivatives or compositions in agriculture or horticulture for controlling or preventing infestation of plants, harvested food crops, seeds or nonliving materials by phytopathogenic microorganisms, preferably fungi.
  • WO 2015/185485 describes the use of substituted oxadiazoles for combating phytopathogenic fungi. Some phenyl oxadiazole derivatives are also known from chemical libraries.
  • a 1 represents N or CR 1 , wherein R is hydrogen, halogen, methyl, ethyl, difluoromethyl, trifluoromethyl, methoxy, ethoxy, or difluoromethoxy;
  • a 2 represents N or CR 2 , wherein R 2 is hydrogen, halogen, methyl, ethyl, difluoromethyl, trifluoromethyl, methoxy, ethoxy, or difluoromethoxy;
  • R 7 represents hydrogen, C 1-6 alkyl, C 3-6 alkenyl, C 3-6 alkynyl, C 1-4 haloalkyl, C 3-6 haloalkenyl, cyanoC 1-6 alkyl, hydroxyC 1-6 alkyl, C 1-4 alkoxyC 1-6 alkyl, C 1-4 haloalkoxyC 1-6 alkyl, C 1-4 alkylcarbonylC 1-4 alkyl, C 1-4 alkoxycarbonyl C 1-4 alkyl, C 1-4 alkylaminocarbonylC 1-4 alkyl, di-C 1-4 alkylaminocarbonylC 1-4 alkyl, C 3- 8 cycloalkyl, C 3-8 cycloalkylC 1-3 alkyl, phenyl, phenylC 1-3 alkyl, heteroaryl, heteroarylC 1-3 alkyl, wherein the heteroaryl moiety is a 5- or 6-membered aromatic ring which comprises 1 , 2, 3 or 4 hetero
  • R 8 represents hydrogen, C 1-6 alkyl, C 3-6 alkenyl, C 3-6 alkynyl, C 1-4 haloalkyl, cyanoC 1-6 alkyl, hydroxyC 1-6 alkyl, C 1-4 alkoxyC 1-6 alkyl, phenyl, or phenylC 1-3 alkyl;
  • R 9 represents cyano, amino, halogen, hydroxy, methyl, ethyl, difluoromethyl, trifluoromethyl, methoxy, ethoxy, difluoromethoxy, C 1-4 alkoxycarbonyl, C 1-4 alkylaminocarbonyl, di-C 1- 4alkylaminocarbonyl, or cyclopropyl; or
  • R 7 and R 8 together with the nitrogen atom and oxygen atom to which they are bonded, respectively, form (i) a 5- or 6-membered cycle optionally containing one additional heteroatom or group selected from O, S, N or NR 0 , wherein R 0 is H or C 1-4 alkyl, or (ii) a 7- to 11 -membered non-aromatic cyclic bridged ring system optionally containing one additional heteroatom or group selected from O, S, N or NR 10 , wherein R 0 is H or C 1-4 alkyl; or a salt or an N-oxide thereof; or a compound of Formula (IB):
  • a 1 is CR 1 , , wherein R is hydrogen
  • a 2 is CR 2 , wherein R 2 is hydrogen
  • R 5 and R 6 independently represent hydrogen or methyl;
  • R 7 represents hydrogen, C 1-6 alkyl, C 3-6 alkenyl, C 3-6 alkynyl, C 1-4 haloalkyl, C 3-6 haloalkenyl, cyanoC 1-6 alkyl, hydroxyC 1-6 alkyl, C 1-4 alkoxyC 1-6 alkyl, C 1-4 haloalkoxyC 1-6 alkyl, C 1-4 alkylcarbonylC 1-4 alkyl, C 1-4 alkoxycarbonylC 1-4 alkyl, C 1-4 alkylaminocarbonylC 1-4 alkyl, di-C 1-4 alkylaminocarbonylC 1-4 alkyl, C 3- 8 cycloalkyl, C3-8cycloalkylC 1-3 alkyl, phenyl, phenylC 1-3 alkyl, heteroaryl, heteroarylC 1-3 alkyl, wherein the heteroaryl moiety is a 5- or 6-membered
  • R 8 represents hydrogen, C 1-6 alkyl, C 3-6 alkenyl, C 3-6 alkynyl, C 1-4 haloalkyl, cyanoC 1-6 alkyl, hydroxyC 1-6 alkyl, C 1-4 alkoxyC 1-6 alkyl, phenyl, or phenylC 1-3 alkyl;
  • R 9 represents cyano, amino, halogen, hydroxy, methyl, ethyl, difluoromethyl, trifluoromethyl, methoxy, ethoxy, difluoromethoxy, C 1-4 alkoxycarbonyl, C 1-4 alkylaminocarbonyl, di-C 1- 4alkylaminocarbonyl, or cyclopropyl; or
  • R 7 and R 8 together with the nitrogen atom and oxygen atom to which they are bonded, respectively, form (i) a 5- or 6-membered cycle optionally containing one additional heteroatom or group selected from O, S, N or NR 0 , wherein R 0 is H or C 1-4 alkyl, or (ii) a 7- to 11 -membered non-aromatic cyclic bridged ring system optionally containing one additional heteroatom or group selected from O, S, N or NR 10 , wherein R 0 is H or C 1-4 alkyl; or a salt or an N-oxide thereof; with the proviso that the compound of Formula (IB) is not:
  • novel compounds of Formula (IA) and (IB) have, for practical purposes, a very advantageous level of biological activity for protecting plants against diseases that are caused by fungi.
  • an agrochemical composition comprising a fungicidally effective amount of a compound of Formula (IA) or (IB).
  • Such an agricultural composition may further comprise at least one additional active ingredient and/or an agrochemically- acceptable diluent or carrier.
  • a method of controlling or preventing infestation of useful plants by phytopathogenic microorganisms wherein a fungicidally effective amount of a compound of Formula (IA) or (IB), or a composition comprising this compound as active ingredient, is applied to the plants, to parts thereof or the locus thereof.
  • a compound of Formula (IA) or (IB) as a fungicide.
  • the use may exclude methods for the treatment of the human or animal body by surgery or therapy.
  • halogen refers to fluorine (fluoro), chlorine (chloro), bromine (bromo) or iodine (iodo), preferably fluorine, chlorine or bromine.
  • C 1-6 alkyl refers to a straight or branched hydrocarbon chain radical consisting solely of carbon and hydrogen atoms, containing no unsaturation, having from one to six carbon atoms, and which is attached to the rest of the molecule by a single bond.
  • C 2-6 alkyl, C 1-4 alkyl, C 1- 3alkyl and C 1-2 alkyl are to be construed accordingly.
  • Examples of C 1-6 alkyl include, but are not limited to, methyl, ethyl, n-propyl, 1-methylethyl (iso-propyl), n-butyl, and 1-dimethylethyl (i-butyl).
  • C 1-6 alkylene refers to the corresponding definition of C 1-6 alkyl (and C 1-4 alkyl and C 1-3 alkyl), except that such radical is attached to the rest of the molecule by two single bonds.
  • Examples of C 1-6 alkylene include, but are not limited to, -CH 2 -, -CH2CH2- and -(CH 2 ) 3 -.
  • cyano means a -CN group.
  • hydroxy means an -OH group.
  • amino means an -NH2 group.
  • C 1-6 alkoxy refers to a radical of the formula -OR a where R a is a C 1- 6alkyl radical as generally defined above. C 1-4 alkoxy and C 1-2 alkoxy are to be construed accordingly. Examples of C 1-6 alkyl include, but are not limited to, methoxy, ethoxy, propoxy, iso-propoxy, and t- butoxy.
  • C 3 -4haloalkyl refers to a C 1-4 alkyl radical as generally defined above substituted by one or more of the same or different halogen atoms.
  • d-2haloalkyl is to be construed accordingly.
  • Examples of d-4haloalkyl include, but are not limited to fluoromethyl, fluoroethyl, difluoromethyl, trifluoromethyl, 2,2-difluoroethyl, and 2,2,2-trifluoroethyl.
  • C 3-6 alkenyl refers to a straight or branched hydrocarbon chain radical group consisting solely of carbon and hydrogen atoms, containing at least one double bond that can be of either the (E)- or (Z)-configu ration, having from three to six carbon atoms, which is attached to the rest of the molecule by a single bond .
  • C 1-4 alkenyl is to be construed accordingly.
  • Examples of C 3 -C 6 alkenyl include, but are not limited to, prop-1-enyl, allyl (prop-2-enyl), and but-1-enyl.
  • C 3-6 alkynyl refers to a straight or branched hydrocarbon chain radical group consisting solely of carbon and hydrogen atoms, containing at least one triple bond , having from three to six carbon atoms, and which is attached to the rest of the molecule by a single bond .
  • C3-4alkynyl is to be construed accordingly.
  • Examples of C 3-6 alkynyl include, but are not limited to, prop- 1-ynyl, propargyl (prop-2-ynyl), and but-1-ynyl.
  • C 3-6 haloalkenyl refers to a C 3-6 alkenyl group as defined above substituted by one or more of the same or different halogen atoms.
  • Examples of C 3-6 haloalkenyl include, but are not limited to 3,3-dichloroallyl, 2,3,3-trichloroallyl, 2,3-dichloroallyl, 3,3-dibromoallyl, 2,3,3- tribromoallyl, and 2,3-dibromoallyl.
  • C 1-4 haloalkoxy refers to a C 1-4 alkoxy group as defined above substituted by one or more of the same or different halogen atoms.
  • C 1-2 haloalkoxy (including C 1- 2fluoroalkoxy) is to be construed accordingly.
  • Examples of C 1-4 haloalkoxy include, but are not limited to, fluoromethoxy, difluoromethoxy, fluoroethoxy, trifluoromethoxy, and trifluoroethoxy.
  • C 1-4 alkoxyC 1-6 alkyl refers to radical of the formula Rb-0-R a - where Rb is a C 1-4 alkyl radical as generally defined above, and R a is a C 1-6 alkylene radical as generally defined above.
  • Rb is a C 1-4 alkyl radical as generally defined above
  • R a is a C 1-6 alkylene radical as generally defined above.
  • C 1-4 alkoxyC 1-4 alkyl and C 1-2 alkoxyC 1-4 alkyl are to be construed accordingly.
  • C 1-4 haloalkoxyC 1-6 alkyl refers to radical of the formula Rb-0-R a - where Rb is a C 1-4 haloalkyl radical as generally defined above, and R a is a C 1-6 alkylene radical as generally defined above.
  • C 1-2 haloalkoxyC 1-4 alkyl is to be construed accordingly.
  • hydroxyC 1-6 alkyl refers to a C 1-6 alkyl radical as generally defined above substituted by one or more hydroxy groups. HydroxyC 1-4 alkyl is to be construed accordingly.
  • cyanoC 1-6 alkyl refers to a C 1-6 alkyl radical as generally defined above substituted by one or more cyano groups. CyanoC 1-4 alkyl is to be construed accordingly.
  • C 1-4 alkylcarbonyl refers to a radical of the formula -C(0)R a where R a is a C 1-4 alkyl radical as generally defined above.
  • C 3-6 alkylcarbonylC 1-4 alkyl refers to a radical of the formula -RbC(0)R a where R a is a C 1-6 alkyl as generally defined above and Rb is a C 1-4 alkylene radical as generally defined above.
  • C 1-4 alkoxycarbonyl refers to a radical of the formula -C(0)OR a where R a is a C 1-4 alkyl radical as generally defined above.
  • C 1-4 alkoxycarbonylC 1-4 alkyl refers to a radical of the formula - RbC(0)OR a , where R a is a C 1-4 alkyl radical as generally defined above and Rb is a C 1-4 alkylene radical as generally defined above.
  • C 1-4 alkylaminocarbonyl refers to a radical of the formula -C(0)NHR a where R a is a C 1-4 alkyl radical as generally defined above.
  • diC 1-4 alkylaminocarbonyl refers to a radical of the formula - C(0)NR a (R a ) where each R a is independently a C 1-4 alkyl radical as generally defined above.
  • C 1-4 alkylaminocarbonylC 1-4 alkyl refers to a radical of the formula - RbC(0)NHR a where R a is a C 1-4 alkyl radical as generally defined above and Rb is C 1-4 alkylene radical as generally defined above.
  • C 3-8 cycloalkyl refers to a stable, monocyclic ring radical which is saturated or partially unsaturated and contains 3 to 8 carbon atoms.
  • C 3-6 cycloalkyl is to be construed accordingly.
  • Examples of d-scycloalkyl include, but are not limited to, cyclopropyl, cyclobutyl, cyclopentyl and cyclohexyl.
  • C 3-8 cycloalkylC 1- 3alkyl refers to a d-scycloalkyl ring as defined above attached to the rest of the molecule by a C 1-8 alkylene radical as defined above.
  • C3- 6cycloalkylC 1-3 alkyl and “C3-4cycloalkylC 1-2 alkyl” are to be construed accordingly.
  • Examples of C3- 8cycloalkylC 1-3 alkyl include, but are not limited to cyclopropyl-methyl, cyclobutyl-ethyl, and cyclopentyl- propyl.
  • phenylC 1-3 alkyl refers to a phenyl ring attached to the rest of the molecule by a C 1-3 alkylene radical as defined above.
  • phenylC2-3alkyl should be construed accordingly. Examples of phenylC 1-3 alkyl include, but are not limited to, benzyl.
  • heteroaryl refers to a 5- or 6-membered monocyclic aromatic ring radical which comprises 1 , 2, 3 or 4 heteroatoms individually selected from nitrogen, oxygen and sulfur.
  • the heteroaryl radical may be bonded to the rest of the molecule via a carbon atom or heteroatom.
  • heteroaryl examples include, but are not limited to, furanyl, pyrrolyl, thienyl, pyrazolyl, imidazolyl, thiazolyl, isothiazolyl, oxazolyl, isoxazolyl, triazolyl, tetrazolyl, pyrazinyl, pyridazinyl, pyrimidyl, pyridyl, and indolyl.
  • heteroarylC 1-3 alkyl refers to a heteroaryl ring as defined above which is attached to the rest of the molecule by a C 1-3 alkylene radical as defined above.
  • heterocyclyl refers to a stable 4-, 5- or 6-membered non-aromatic monocyclic ring radical or a 7- to 11-membered non-aromatic bridged ring system, which comprises 1 , 2, or 3 heteroatoms individually selected from nitrogen, oxygen and sulfur.
  • the heterocyclyl radical may be bonded to the rest of the molecule via a carbon atom or heteroatom.
  • heterocyclyl examples include, but are not limited to, pyrrolinyl, pyrrolidyl, tetrahydrofuranyl, tetrahydrothienyl, tetrahydrothiopyranyl, piperidyl, piperazinyl, tetrahydropyranyl, dioxolanyl, morpholinyl, ⁇ -lactamyl, perhydroazepinyl, indolinyl, benzimidazole, oxetanyl, isoxazolidinyl, oxazinanyl, 3-oxa-2- azabicylo[2.2.2]octanyl, and 3-oxa-2-azabicylo[2.2.2]octenyl.
  • examples of heterocyclyl are piperidyl and tetrahydropyranyl.
  • heterocyclylC 1-3 alkyl refers to a heterocyclic ring as defined above which is attached to the rest of the molecule by a C 1-3 alkylene radical as defined above.
  • heterocyclyloxyd-3alkyl refers to a heterocyclic ring as defined above bound to an oxygen through a ring carbon, wherein the oxygen is attached to the rest of the molecule by a C 1-3 alkylene radical as defined above.
  • the presence of one or more possible asymmetric carbon atoms in a compound of Formula (IA) or (IB) means that the compounds may occur in chiral isomeric forms, i.e., enantiomeric or diastereomeric forms. Also atropisomers may occur as a result of restricted rotation about a single bond.
  • Formulas (IA) and (IB) are intended to include all those possible isomeric forms and mixtures thereof.
  • the present invention includes all those possible isomeric forms and mixtures thereof for compounds of Formula (IA) and (IB).
  • Formulas (IA) and (IB) are intended to include all possible tautomers (including lactam-lactim tautomerism and keto-enol tautomerism) where present.
  • the present invention includes all possible tautomeric forms for a compound of Formula (I).
  • the compounds of Formula (IA) and (IB) according to the invention are in free form, in oxidized form as an N-oxide, in covalently hydrated form, or in salt form, e.g. , an agronomically usable or agrochemically acceptable salt form.
  • N-oxides are oxidized forms of tertiary amines or oxidized forms of nitrogen containing heteroaromatic compounds. They are described for instance in the book "Heterocyclic N-oxides" by A. Albini and S. Pietra, CRC Press, Boca Raton 1991.
  • Each of these aforementioned compounds not according to the invention may be used in a method of controlling or preventing infestation of useful plants by phytopathogenic microorganisms, wherein a fungicidally effective amount of the compound or a composition comprising the compound as active ingredient is applied to the plants, to parts thereof or the locus thereof.
  • the aforementioned compounds not according to the invention may be useful as fungicidal agents.
  • the following list provides definitions, including preferred definitions, for substituents n, A 1 , A 2 , R 1 , R 2 , R 3 , R 4 , R 5 , R 6 , R 7 , R 8 , R 9 and R 0 , with reference to the compounds of Formula (IA) according to the invention.
  • any of the definitions given below may be combined with any definition of any other substituent given below or elsewhere in this document.
  • a 1 represents N or CR 1 , wherein R is hydrogen, halogen, methyl, ethyl, difluoromethyl, trifluoromethyl, methoxy, ethoxy, or difluoromethoxy.
  • R is selected from hydrogen, halogen or methyl. More preferably, R is hydrogen, fluoro or methyl. Most preferably, R is hydrogen or fluoro.
  • a 2 represents N or CR 2 , wherein R 2 is hydrogen, halogen, methyl, ethyl, difluoromethyl, trifluoromethyl, methoxy, ethoxy, or difluoromethoxy.
  • R 2 represents N or CR 1 , wherein R is selected from hydrogen, halogen or methyl. More preferably, R 2 is hydrogen, fluoro or methyl, and most preferably, hydrogen.
  • R 3 represents hydrogen or halogen. Preferably, R 3 is hydrogen or fluoro.
  • R 4 represents hydrogen or halogen.
  • R 4 is hydrogen or fluoro, and most preferably hydrogen.
  • R 3 and R 4 are both hydrogen.
  • a 1 is CR 1 and A 2 is CR 2 , 0, 1 , 2, or 3 of R to R 4 are hydrogen.
  • a 1 is CR 1 and A 2 is CR 2 , 2 or 3 of R to R 4 are hydrogen. More preferably, when A 1 is CR 1 and A 2 is CR 2 , 3 of R to R 4 are hydrogen.
  • a 1 is CR 1 and R is halogen and preferably fluorine
  • a 2 is CR 2 and R 2 is hydrogen
  • R 3 and R 4 are hydrogen
  • a 1 is CR 1 and R is hydrogen
  • a 2 is CR 2 and R 2 is hydrogen
  • R 3 is halogen and preferably fluorine
  • R 4 is hydrogen
  • a 1 is N
  • a 2 is CR 2 and R 2 is hydrogen
  • R 3 and R 4 are hydrogen.
  • n represents 0 or 1. In some embodiments of the invention, n is 0. In other embodiments of the invention, n is 1.
  • R 5 and R 6 independently represent hydrogen or methyl.
  • R 5 and R 6 are both hydrogen.
  • R 7 represents hydrogen, C 1-6 alkyl, C 3-6 alkenyl, C 3-6 alkynyl, C 1-4 haloalkyl, C 3-6 haloalkenyl, cyanoC 1-6 alkyl, hydroxyC 1-6 alkyl, C 1-4 alkoxyC 1-6 alkyl, C 1-4 haloalkoxyC 1-6 alkyl, C 1-4 alkylcarbonylC 1-4 alkyl, C 1-4 alkoxycarbonylC 1-4 alkyl, C 1-4 alkylaminocarbonylC 1-4 alkyl, di-C 1-4 alkylaminocarbonylC 1-4 alkyl, C3- ecycloalkyl, C3-8cycloalkylC 1-3 alkyl, phenyl, phenylC 1-3 alkyl, heteroaryl, heteroarylC 1-3 alkyl, wherein the heteroary
  • R 7 is selected from hydrogen, C 1-6 alkyl, C 3-6 alkynyl, C 1-4 haloalkyl, hydroxyC 1-6 alkyl, C3-8cycloalkyl, C3-8cycloalkylC 1-3 alkyl, phenyl, phenylC 1-3 alkyl, heteroaryl, heteroarylC 1-3 alkyl, heterocyclyl, heterocyclylC 1-3 alkyl, or heterocyclyloxyC 1-3 alkyl, wherein any of said cycloalkyl, phenyl and heterocyclyl moieties are optionally substituted by 1 , 2 or 3 substituents, which may be the same or different, selected from R 9 .
  • R 7 is selected from hydrogen, C 1-4 alkyl, C3-4alkynyl, C 1-2 haloalkyl, hydroxyd- 4alkyl, C 3-6 cycloalkyl, C 3-6 cycloalkylC 1-3 alkyl, phenyl, phenylC 1-3 alkyl, furanyl, furanylC 1-3 alkyl, piperidinyl, piperidinylC 1-3 alkyl, or tetrahydropyranyloxyC 1-3 alkyl, wherein any of said cycloalkyl, phenyl, furanyl, piperidinyl and tetrahydropyranyl moieties are optionally substituted by 1 , 2 or 3 substituents, which may be the same or different, selected from R 9 .
  • R 7 is hydrogen, methyl, 2,2-difluoroethyl, (2,4,6-trichlorophenyl)methyl, 1-methyl-2-(2,4,6-trichlorophenyl)ethyl, benzyl, N-methoxy-4-methoxycarbonyl-piperidin-4-yl, furan-2- ylmethyl, cyclopropyl-methyl, 1-methyl-2-(tetrahydropyran-2-yloxy)ethyl, prop-2-ynyl, or 2-hydroxy-1- m ethyl-ethyl.
  • R 7 represents C 3-6 alkenyl, C 3-6 alkynyl, C 1-
  • R 7 is selected from C3- 6alkynyl, hydroxyC 1-6 alkyl, C 3-6 cycloalkyl, C 3-6 cycloalkylC 1-3 alkyl, phenyl, phenylC 1-3 alkyl, heteroaryl, heteroarylC 1-3 alkyl, heterocyclyl, heterocyclylC 1-3 alkyl, or heterocyclyloxyC 1-3 alkyl, wherein any of said cycloalkyl, phenyl and heterocyclyl moieties are optionally substituted by 1 , 2 or 3 substituents, which may be the same or different, selected from R 9 .
  • each cycloalkyl, phenyl, heteroaryl or heterocyclyl is optionally substituted by 1 , 2, 3 or 4 substituents, which may be the same or different, selected from R 9 .
  • each cycloalkyl, phenyl, heteroaryl or heterocyclyl is optionally substituted by 1 , 2 or 3 substituents, which may be the same or different, selected from R 9 .
  • each cycloalkyl, phenyl, heteroaryl or heterocyclyl is optionally substituted by 1 or 2 substituents, which may be the same or different, selected from R 9 .
  • R 7 comprises a cycloalkyl, phenyl, heteroaryl or heterocyclyl moiety, each cycloalkyl, phenyl, heteroaryl or heterocyclyl is optionally substituted by a single substituent selected from R 9 .
  • R 8 represents hydrogen, C 1-6 alkyl, C 3-6 alkenyl, C 3-6 alkynyl, C 1-4 haloalkyl, cyanoC 1-6 alkyl, hydroxyC 1-6 alkyl, C 1-4 alkoxyC 1-6 alkyl, phenyl or phenylC 1-3 alkyl.
  • R 8 represents hydrogen, C 1-4 alkyl, C3- 6alkenyl, cyanoC 1-6 alkyl, phenyl, or phenylC 1-3 alkyl.
  • R 8 represents hydrogen, methyl, ethyl, prop-1-enyl, 1-methyl-2-cyano-ethyl or benzyl. Most preferably, R 8 is methyl.
  • R 8 represents hydrogen, C 3-6 alkenyl, C 3-6 alkynyl, C 1-
  • R 8 represents hydrogen, prop-1-enyl, 1-methyl-2-cyano-ethyl or benzyl.
  • R 9 represents cyano, amino, halogen, hydroxy, methyl, ethyl, difluoromethyl, trifluoromethyl, methoxy, ethoxy, difluoromethoxy, C 1-4 alkoxycarbonyl, C 1-4 alkylaminocarbonyl, di-C 1- 4alkylaminocarbonyl, or cyclopropyl.
  • R 9 represents halogen, methoxy and C 1- 4alkoxycarbonyl. More preferably, R 9 represents chloro, methoxy and methoxycarbonyl.
  • R 7 and R 8 together with the nitrogen atom and oxygen atom to which they are bonded, respectively, form (i) a 5- or 6-membered cycle optionally containing one additional heteroatom or group selected from O, S, N or NR 0 , wherein R 0 is H or C 1-4 alkyl, or (ii) a 7- to 11-membered non-aromatic cyclic bridged ring system optionally containing one additional heteroatom or group selected from O, S, N or NR 10 , wherein R 0 is H or C 1-4 alkyl, in particular isoxazolidinyl, oxazinanyl, 3-oxa-2- azabicyclo[2.2.2]octanyl, and 3-oxa-2-azabicyclo[2.2.2]oct-5-enyl.
  • R 7 and R 8 together with the nitrogen atom and oxygen atom to which they are bonded, respectively, form an isoxazolidinyl or oxazinany
  • a 1 is CR 1 , wherein R is hydrogen.
  • a 2 is CR 2 , wherein R 2 is hydrogen. R 3 and R 4 are both hydrogen. n represents 0 or 1. In some embodiments of the invention, n is 0. In other embodiments of the invention, n is 1.
  • R 5 and R 6 independently represent hydrogen or methyl.
  • R 5 and R 6 are each independently hydrogen.
  • R 7 represents hydrogen, C 1-6 alkyl, C 3-6 alkenyl, C 3-6 alkynyl, C 1-4 haloalkyl, C 3-6 haloalkenyl, cyanoC 1-6 alkyl, hydroxyC 1-6 alkyl, C 1-4 alkoxyC 1-6 alkyl, C 1-4 haloalkoxyC 1-6 alkyl, C 1-4 alkylcarbonylC 1-4 alkyl, C 1-4 alkoxycarbonylC 1-4 alkyl, C 1-4 alkylaminocarbonylC 1-4 alkyl, di-C 1-4 alkylaminocarbonylC 1-4 alkyl, C3- ecycloalkyl, C3-8cycloalkylC 1-3 alkyl, phenyl, phenylC 1-3 alkyl, heteroaryl, heteroarylC 1-3 alkyl, wherein the hetero
  • R 7 represents hydrogen, C 1-6 alkyl, C 3-6 alkenyl, C 3-6 alkynyl, C 1-4 haloalkyl, C3-
  • R 7 represents hydrogen, C 1-4 alkyl, C 1-4 alkenyl, C 1-4 alkynyl, d-4haloalkyl, C3- 4haloalkenyl, C 1-4 alkoxycarbonylC 1-4 alkyl, C 1-4 alkylaminocarbonylC 1-4 alkyl, phenyl, phenylC 1-3 alkyl, piperidinyl or piperidinylC 1-3 alkyl, wherein any of said phenyl and piperidinyl moieties are optionally substituted by 1 , 2 or 3 substituents, which may be the same or different, selected from R 9 ;
  • R 7 represents hydrogen, 2,2-difluoroethyl, benzyl, prop-2-enyl, prop-2- ynl, 3,3-dichloroprop-2-enyl, (methoxycarbonyl)methyl, (l-methoxycarbonyl)ethyl, N-methoxy-4- methoxycarbonyl-piperidin-4-yl, 2-(tert-butylaminocarbonyl)ethyl, and 1-methyl-(2- m ethoxycarbonyl)ethyl .
  • R 7 represents C2-4alkyl, C 3-6 alkenyl, C3- 6alkynyl, C 1-4 haloalkyl, C 3-6 haloalkenyl, cyanoC 1-6 alkyl, hydroxyC 1-6 alkyl, C 1-4 alkoxyC 1-6 alkyl, C 1- 4haloalkoxyC 1-6 alkyl, C 1-4 alkylcarbonylC 1-4 alkyl, C 1-4 alkoxycarbonylC 1-4 alkyl, C 1-4 alkylaminocarbonylC 1- 4alkyl, di-C 1-4 alkylaminocarbonylC 1-4 alkyl, C 3-6 cycloalkyl, C 3-6 cycloalkylC 1-3 alkyl, phenyl, phenylCi salkyl, heteroaryl, heteroarylC 1-3 alkyl, wherein the heteroaryl moiety is a 5- or 6-membered aromatic
  • R 7 represents C3- 6alkenyl, C 3-6 alkynyl, C 3-6 haloalkenyl, C 1-4 alkoxycarbonylC 1-4 alkyl, C 1-4 alkylaminocarbonylC 1-4 alkyl, phenyl, phenylC 1-3 alkyl, heterocyclyl or heterocyclylC 1-3 alkyl, wherein any of said phenyl and heterocyclyl moieties are optionally substituted by 1 , 2 or 3 substituents, which may be the same or different, selected from R 9 .
  • each cycloalkyi, phenyl, heteroaryl or heterocyclyl is optionally substituted by 1 , 2, 3 or 4 substituents, which may be the same or different, selected from R 9 .
  • each cycloalkyi, phenyl, heteroaryl or heterocyclyl is optionally substituted by 1 , 2 or 3 substituents, which may be the same or different, selected from R 9 .
  • each cycloalkyi, phenyl, heteroaryl or heterocyclyl is optionally substituted by 1 or 2 substituents, which may be the same or different, selected from R 9 .
  • R 7 comprises a cycloalkyi, phenyl, heteroaryl or heterocyclyl moiety, each cycloalkyi, phenyl, heteroaryl or heterocyclyl is optionally substituted by a single substituent selected from R 9 .
  • R 8 represents hydrogen, C 1-6 alkyl, C 3-6 alkenyl, C 3-6 alkynyl, C 1-4 haloalkyl, cyanoC 1-6 alkyl, hydroxyC 1-6 alkyl, C 1-4 alkoxyC 1-6 alkyl, phenyl or phenylC 1-3 alkyl.
  • R 8 represents hydrogen, C 1- 6alkyl, C 3-6 alkenyl and C 3-6 alkynyl. More preferably, R 8 represents hydrogen, methyl, ethyl, prop-1-ynyl, prop-1-enyl, or benzyl. Most preferably, R 8 is methyl.
  • R 8 represents hydrogen, C 3-6 alkenyl, C 3-6 alkynyl, C 1- 4haloalkyl, cyanoC 1-6 alkyl, hydroxyC 1-6 alkyl, C 1-4 alkoxyC 1-6 alkyl, phenyl or phenylC 1-3 alkyl.
  • R 8 represents hydrogen, C 3-6 alkenyl, cyanoC 1-6 alkyl, phenyl, or phenylC 1-3 alkyl. More preferably, R 8 represents hydrogen, prop-1-enyl, 1-methyl-2-cyano-ethyl or benzyl.
  • R 9 represents cyano, amino, halogen, hydroxy, methyl, ethyl, difluoromethyl, trifluoromethyl, methoxy, ethoxy, difluoromethoxy, C 1-4 alkoxycarbonyl, C 1-4 alkylaminocarbonyl, di-C 1- 4alkylaminocarbonyl, or cyclopropyl.
  • R 9 is independently selected from methoxy and C 1- 4alkoxycarbonyl. More preferably, R 9 is independently selected from methoxy and methoxycarbonyl.
  • R 7 and R 8 together with the nitrogen atom and oxygen atom to which they are bonded, respectively, form (i) a 5- or 6-membered cycle optionally containing one additional heteroatom or group selected from O, S, N or NR 0 , wherein R 0 is H or C 1-4 alkyl, or (ii) a 7- to 11-membered non-aromatic cyclic bridged ring system optionally containing one additional heteroatom or group selected from O, S, N or NR 10 , wherein R 0 is H or C 1-4 alkyl, in particular isoxazolidinyl, oxazinanyl, 3-oxa-2- azabicyclo[2.2.2]octanyl, and 3-oxa-2-azabicyclo[2.2.2]oct-5-enyl.
  • R 7 and R 8 together with the nitrogen atom and oxygen atom to which they are bonded, respectively, form an isoxazolidinyl or oxazinanyl.
  • the compound according to Formula (IA) is selected from a compound 1.1 to 1.27 listed in Table T1 (below), and the compound according to Formula (IB) is selected from a compound 2.1 to 2.26 listed in Table T2 (below).
  • n is 0 or 1 ;
  • a 1 is CR and R is halogen and preferably fluorine, A 2 is CR 2 and R 2 is hydrogen, and R 3 and R 4 are hydrogen; or A 1 is CR 1 and R is hydrogen, A 2 is CR 2 and R 2 is hydrogen; R 3 is halogen and preferably fluorine, and R 4 is hydrogen;
  • R 5 and R 6 both represent hydrogen (when n is 1 );
  • R 7 is selected from hydrogen, C 1-6 alkyl, C 3-6 alkynyl, C 1-4 haloalkyl, hydroxyC 1-6 alkyl, C3-scycloalkyl,
  • R 8 is selected from hydrogen, C 1-4 alkyl, C 3-6 alkenyl, cyanoC 1-6 alkyl, phenyl, or phenylC 1-3 alkyl;
  • R 9 represents cyano, amino, halogen, hydroxy, methyl, ethyl, difluoromethyl, trifluoromethyl, methoxy, ethoxy, difluoromethoxy, C 1-4 alkoxycarbonyl, C 1-4 alkylaminocarbonyl, or di-C 1- 4alkylaminocarbonyl;
  • R 7 and R 8 together with the nitrogen atom and oxygen atom to which they are bonded, respectively, form (i) a 5- or 6-membered cycle optionally containing one additional heteroatom or group selected from O, S, N or NR 0 , wherein R 0 is H or C 1-4 alkyl, or (ii) a 7- to 11-membered non-aromatic cyclic bridged ring system optionally containing one additional heteroatom or group selected from O, S, N or NR 10 , wherein R 0 is H or C 1-4 alkyl.
  • n 0.
  • a 1 is CR 1 and R is halogen and preferably fluorine, A 2 is CR 2 and R 2 is hydrogen, and R 3 and R 4 are hydrogen; or A 1 is CR 1 and R is hydrogen, A 2 is CR 2 and R 2 is hydrogen; R 3 is halogen and preferably fluorine, and R 4 is hydrogen;
  • R 7 is selected from hydrogen, C 1-4 alkyl, C3-4alkynyl, C 1-4 haloalkyl, hydroxyC 1-4 alkyl, C 3-6 cycloalkyl, C 3-6 cycloalkylC 1-3 alkyl, phenyl, phenylC 1-3 alkyl, furanyl, furanylC 1-3 alkyl, piperidinyl, piperidinylC 1-
  • R 8 is selected from hydrogen, C 1-4 alkyl, C 3-6 alkenyl, cyanoC 1-6 alkyl, phenyl, or phenylC 1-3 alkyl;
  • R 9 is selected from halogen, C 1-4 alkoxy and C 1-4 alkoxycarbonyl
  • R 7 and R 8 together with the nitrogen atom and oxygen atom to which they are bonded, respectively, form an isoxazolidinyl or oxazinanyl.
  • n is 0.
  • a 1 is CR and R is halogen and preferably fluorine
  • a 2 is CR 2 and R 2 is hydrogen, and R 3 and R 4 are hydrogen
  • a 1 is CR 1 and R is hydrogen, A 2 is CR 2 and R 2 is hydrogen
  • R 3 is halogen and preferably fluorine
  • R 4 is hydrogen
  • R 7 is selected from hydrogen, C 1-4 alkyl, C 1-2 haloalkyl,C3-4alkynyl, hydroxyC 1-4 alkyl, C 3-6 cycloalkyl, C 3-6 cycloalkylC 1-3 alkyl, phenyl, phenylC 1-3 alkyl, furanyl, furanylC 1-3 alkyl, piperidinyl, piperidinylC 1-
  • R 8 is selected from hydrogen or C 1-4 alkyl (preferably, methyl).
  • R 9 is selected from halogen, C 1-4 alkoxy and C 1-4 alkoxycarbonyl.
  • n 0.
  • a 1 is CR 1 and R is halogen and preferably fluorine, A 2 is CR 2 and R 2 is hydrogen, and R 3 and R 4 are hydrogen; or A 1 is CR 1 and R is hydrogen, A 2 is CR 2 and R 2 is hydrogen; R 3 is halogen and preferably fluorine, and R 4 is hydrogen;
  • R 7 is selected from hydrogen, C 1-4 alkyl, C 1-2 haloalkyl,C3-4alkynyl, hydroxyC 1-4 alkyl, C 3-6 cycloalkyl, C 3-6 cycloalkylC 1-3 alkyl, phenyl, phenylC 1-3 alkyl, furanyl, furanylC 1-3 alkyl, piperidinyl, piperidinylC 1- 3alkyl, or tetrahydropyranyloxyC 1-3 alkyl wherein any of said cycloalkyl, phenyl, furanyl, piperidinyl and tetrahydropyranyl moieties are optionally substituted by 1 , 2 or 3 substituents, which may be the same or different, selected from R 9 ;
  • R 8 is selected from hydrogen, C 3-6 alkenyl, cyanoC 1-6 alkyl, phenyl, or phenylC 1-3 alkyl; and R 9 is selected from halogen, C 1-4 alkoxy and C 1-4 alkoxycarbonyl.
  • n is 0 or 1 ;
  • a 1 is CR 1 , wherein R is hydrogen
  • a 2 is CR 2 , wherein R 2 is hydrogen
  • R 3 and R 4 both represent hydrogen
  • R 5 and R 6 both represent hydrogen (when n is 1 );
  • R 7 is selected from hydrogen, C 1-6 alkyl, C 1-4 haloalkyl, C 3-6 alkenyl, C 3-6 alkynyl, C 3-6 haloalkenyl, C 1- 4alkoxycarbonylC 1-4 alkyl, C 1-4 alkylaminocarbonylC 1-4 alkyl, phenyl, phenylC 1-3 alkyl, heterocyclyl or heterocyclylC 1-3 alkyl, wherein any of said phenyl and heterocyclyl moieties are optionally substituted by 1 , 2 or 3 substituents, which may be the same or different, selected from R 9 ;
  • R 8 is selected from hydrogen, C 1-4 alkyl, C 3-6 alkenyl, C 3-6 alkynyl, phenyl or phenylC 1-3 alkyl;
  • R 9 is selected from methoxy and methoxycarbonyl
  • R 7 and R 8 together with the nitrogen atom and oxygen atom to which they are bonded, respectively, form (i) a 5- or 6-membered cycle optionally containing one additional heteroatom or group selected from O, S, N or NR 0 , wherein R 0 is H or C 1-4 alkyl, or (ii) a 7- to 11-membered non-aromatic cyclic bridged ring system optionally containing one additional heteroatom or group selected from O, S, N or NR 10 , wherein R 0 is H or C 1-4 alkyl. More preferably, in a compound according to Formula (IB) of the invention, n is 0 or 1 ;
  • a 1 is CR 1 , wherein R is hydrogen
  • a 2 is CR 2 , wherein R 2 is hydrogen
  • R 3 and R 4 both represent hydrogen
  • R 5 and R 6 both represent hydrogen (when n is 1 );
  • R 7 is selected from hydrogen, C 1-4 alkyl, C 1-2 haloalkyl, C3-4alkenyl, C3-4alkynyl, C3-4haloalkenyl, C 1-
  • R 8 is selected from hydrogen, methyl, ethyl, prop-1-enyl, prop-1-ynyl, and benzyl;
  • R 9 is selected from methoxy and methoxycarbonyl
  • R 7 and R 8 together with the nitrogen atom and oxygen atom to which they are bonded , respectively, form a 3-oxa-2-azabicyclo[2.2.2]octanyl or 3-oxa-2-azabicyclo[2.2.2]oct-5-enyl.
  • n is 0 or 1 ;
  • a 1 is CR 1 , wherein R is hydrogen
  • a 2 is CR 2 , wherein R 2 is hydrogen
  • R 3 and R 4 both represent hydrogen
  • R 5 and R 6 both represent hydrogen (when n is 1 );
  • R 7 is selected from hydrogen, C 1-4 alkyl, C3-4alkenyl, C3-4alkynyl, C 1-4 haloalkyl, C3-4haloalkenyl, C 1- 4alkoxycarbonylC 1-4 alkyl, C 1-4 alkylaminocarbonylC 1-4 alkyl, phenyl, phenylC 1-3 alkyl, piperidinyl or piperidinylC 1-3 alkyl wherein any of said phenyl and piperidinyl moieties are optionally substituted by 1 , 2 or 3 substituents, which may be the same or different, selected from R 9 ;
  • R 8 is selected from hydrogen, methyl or ethyl
  • R 9 is selected from methoxy and methoxycarbonyl.
  • n is 0 or 1 ;
  • a 1 is CR 1 , wherein R is hydrogen;
  • a 2 is CR 2 , wherein R 2 is hydrogen
  • R 3 and R 4 both represent hydrogen
  • R 5 and R 6 both represent hydrogen (when n is 1 );
  • R 7 is selected from hydrogen, C 1-4 alkyl, C3-4alkenyl, C3-4alkynyl, C 1-4 haloalkyl, C3-4haloalkenyl, C 1- 4alkoxycarbonylC 1-4 alkyl, C 1-4 alkylaminocarbonylC 1-4 alkyl, phenyl, phenylC 1-3 alkyl, piperidinyl or piperidinylC 1-3 alkyl wherein any of said phenyl and piperidinyl moieties are optionally substituted by 1 , 2 or 3 substituents, which may be the same or different, selected from R 9 ;
  • R 8 is selected from hydrogen, prop-1-enyl, prop-1-ynyl, and benzyl;
  • R 9 is selected from methoxy and methoxycarbonyl.
  • the compounds of Formula (IA) and Formula (IB) according to the invention may be present in a reversible equilibrium with the corresponding covalently hydrated forms (e.g., as represented by the compounds of Formula (IA-I) and Formula (IA-II) or the compounds of Formula (IB-I) and Formula (IB-II), which may exist in tautomeric form as the compounds of Formula ( ⁇ -la) and Formula (IA-lla) or Formula (IB-la) and Formula (IB-lla), at the CF3-oxadiazole motif.
  • This dynamic equilibrium may be important for the biological activity of the compounds of Formula (I), (respectively, as shown below) at the CF3-oxadiazole motif. This dynamic equilibrium may be important for the biological activity of the compounds of Formula (IA) and Formula (IB).
  • n A 1 , A 2 , R 1 , R 2 , R 3 , R 4 , R 5 , R 6 , R 7 , R 8 , R 9 and R 0
  • the designations of n, A 1 , A 2 , R 1 , R 2 , R 3 , R 4 , R 5 , R 6 , R 7 , R 8 , R 9 and R 0 apply generally to the compounds of Formula (IA-I) and Formula (IA-II), as well as to the specific disclosures of combinations of n, A 1 , A 2 , R , R 2 , R 3 , R 4 , R 5 , R 6 , R 7 , R 8 , R 9 and R 0 , as represented for compounds of Formula (IA) in Tables 1 .1 A to 1.25A (below), or the compounds 1.1 to 1.27 described in Table T1 (below).
  • n A 1 , A 2 , R 1 , R 2 , R 3 , R 4 , R 5 , R 6 , R 7 , R 8 , R 9 and R 0
  • the designations of n, A 1 , A 2 , R 1 , R 2 , R 3 , R 4 , R 5 , R 6 , R 7 , R 8 , R 9 and R 0 apply generally to the compounds of Formula (IB-I) and Formula (IB-II), as well as to the specific disclosures of combinations of n, A 1 , A 2 , R , R 2 , R 3 , R 4 , R 5 , R 6 , R 7 , R 8 , R 9 and R 0 , as represented for compounds of Formula (IB) in Tables 1.1 B to 1 .1 OB (below), or the compounds 2.1 to 2.26 described in Table T2 (below).
  • the compounds of Formula (I) can be obtained by an amide coupling transformation with compounds of Formula (II) and compounds of Formula (III) by activating the carboxylic acid function of the compounds of Formula (III), a process that usually takes place by converting the -OH of the carboxylic acid into a good leaving group, such as a chloride group, for example by using (COCI)2 or SOCI2, prior to treatment with the compounds of Formula (II), preferably in a suitable solvent (e.g., dimethylformamide, dichloromethane or tetrahydrofuran), preferably at a temperature of between 25°C and 100°C, and optionally in the presence of a base such as triethylamine or N-N-diisopropylethylamine, or under conditions described in the literature for an amide coupling.
  • a suitable solvent e.g., dimethylformamide, dichloromethane or tetrahydrofuran
  • a base such as triethylamine or N-
  • compounds of Formula (I) (R 7 is not hydrogen) can be prepared from compounds of Formula (I) (R 7 is hydrogen) and compounds of Formula (IV), wherein X is chlorine, bromine or iodine, by treatment with a base (e.g., K2CO3 or CS2CO3) in a suitable solvent, such as acetone or acetonitrile, at a temperature between 0°C and 50°C.
  • a base e.g., K2CO3 or CS2CO3
  • suitable solvent such as acetone or acetonitrile
  • compounds of Formula (I) can be prepared from compounds of Formula (V) by treatment with trifluoroacetic anhydride, trifluoroacetyl fluoride, or trifluoroacetyl chloride in a suitable solvent, such as tetrahydrofuran, optionally in the presence of a base, such as pyridine, at a temperature between 0°C and 25°C.
  • a suitable solvent such as tetrahydrofuran
  • a base such as pyridine
  • Compounds of Formula (V) can be prepared from compounds of Formula (VI) by treating them with a hydroxyamine hydrochloride salt in the presence of a base, such as sodium carbonate, in a suitable solvent, such as methanol, at a temperature between 0°C and 100°C.
  • a base such as sodium carbonate
  • a suitable solvent such as methanol
  • the compounds of Formula (VI) can be obtained by an amide coupling transformation with compounds of Formula (II) and compounds of Formula (VII) by activating the carboxylic acid function of the compounds of Formula (VII), a process that usually takes place by converting the -OH of the carboxylic acid into a good leaving group, such as a chloride group, for example by using (COCI)2 or SOCI2, prior to treatment with the compounds of Formula (II), preferably in a suitable solvent (e.g., dimethylformamide, dichloromethane or tetrahydrofuran), preferably at a temperature of between 25°C and 100°C, and optionally in the presence of a base such as triethylamine or A/,A/-diisopropylethylamine, or under conditions described in the literature for an amide coupling.
  • a suitable solvent e.g., dimethylformamide, dichloromethane or tetrahydrofuran
  • a base such as triethyl
  • Compounds of Formula (III) can be prepared from compounds of Formula (VIII) by treatment with trifluoroacetic anhydride, trifluoroacetyl fluoride, or trifluoroacetyl chloride in a suitable solvent, such as tetrahydrofuran, optionally in the presence of a base, such as pyridine, at a temperature between 0°C and 25°C.
  • a suitable solvent such as tetrahydrofuran
  • a base such as pyridine
  • Compounds of Formula (VIII) can be prepared from compounds of Formula (VII) by treating them with a hydroxyamine hydrochloride salt in the presence of a base, such as sodium carbonate, in a suitable solvent, such as methanol, at a temperature between 0°C and 100°C.
  • a base such as sodium carbonate
  • a suitable solvent such as methanol
  • novel compounds of Formula (lA) and (IB) of the present invention have, for practical purposes, a very advantageous level of biological activity for protecting plants against diseases that are caused by fungi.
  • the compounds of Formula (IA) and (IB) can be used in the agricultural sector and related fields of use, e.g., as active ingredients for controlling plant pests or on non-living materials for the control of spoilage microorganisms or organisms potentially harmful to man.
  • the novel compounds are distinguished by excellent activity at low rates of application, by being well tolerated by plants and by being environmentally safe. They have very useful curative, preventive and systemic properties and can be used for protecting numerous cultivated plants.
  • the compounds of Formula (IA) and (IB) can be used to inhibit or destroy the pests that occur on plants or parts of plants (fruit, blossoms, leaves, stems, tubers, roots) of different crops of useful plants, while at the same time protecting also those parts of the plants that grow later, e.g., from phytopathogenic microorganisms.
  • the present invention further relates to a method for controlling or preventing infestation of plants or plant propagation material and/or harvested food crops susceptible to microbial attack by treating plants or plant propagation material and/or harvested food crops wherein an effective amount a compound of Formula (IA) or (IB) is applied to the plants, to parts thereof or the locus thereof.
  • fungicide as used herein means a compound that controls, modifies, or prevents the growth of fungi.
  • fungicidally effective amount where used means the quantity of such a compound or combination of such compounds that is capable of producing an effect on the growth of fungi. Controlling or modifying effects include all deviation from natural development, such as killing, retardation and the like, and prevention includes barrier or other defensive formation in or on a plant to prevent fungal infection.
  • compositions comprising a compound of Formula (IA) or (IB) before planting: seed, for example, can be dressed before being sown.
  • the active compounds of Formula (IA) and (IB) can also be applied to grains (coating), either by impregnating the seeds in a liquid formulation or by coating them with a solid formulation.
  • the composition can also be applied to the planting site when the propagation material is being planted, for example, to the seed furrow during sowing.
  • the invention relates also to such methods of treating plant propagation material and to the plant propagation material so treated.
  • the compounds of Formula (IA) and (IB) can be used for controlling fungi in related areas, for example in the protection of technical materials, including wood and wood related technical products, in food storage, in hygiene management.
  • the invention could be used to protect non-living materials from fungal attack, e.g. lumber, wall boards and paint.
  • the compounds of Formula (IA) and (IB) are for example, effective against fungi and fungal vectors of disease as well as phytopathogenic bacteria and viruses.
  • These fungi and fungal vectors of disease as well as phytopathogenic bacteria and viruses are for example:
  • Absidia corymbifera Alternaria spp, Aphanomyces spp, Ascochyta spp, Aspergillus spp. including A. flavus, A. fumigatus, A. nidulans, A. niger, A. terms, Aureobasidium spp. including A. pullulans, Blastomyces dermatitidis, Blumeria graminis, Bremia lactucae, Botryosphaeria spp. including B. dothidea, B. obtusa, Botrytis spp. comprising B. cinerea, Candida spp. including C. albicans, C. glabrata, C. krusei, C.
  • Penicillium spp. including P. digitatum, P. italicum, Petriellidium spp, Peronosclerospora spp. Including P. maydis, P. philippinensis and P. sorghi, Peronospora spp, Phaeosphaeria nodorum, Phakopsora pachyrhizi, Phellinus igniarus, Phialophora spp, Phoma spp, Phomopsis viticola, Phytophthora spp.
  • P. infestans Plasmopara spp. including P. halstedii, P. viticola, Pleospora spp., Podosphaera spp. including P. leucotricha, Polymyxa graminis, Polymyxa betae, Pseudocercosporella herpotrichoides, Pseudomonas spp, Pseudoperonospora spp. including P. cubensis, P. humuli, Pseudopeziza tracheiphila, Puccinia Spp. including P. hordei, P. recondita, P. striiformis, P.
  • the compounds of Formula (IA) and (IB) may be used for example on turf, ornamentals, such as flowers, shrubs, broad-leaved trees or evergreens, for example conifers, as well as for tree injection, pest management and the like.
  • target crops and/or useful plants to be protected typically comprise perennial and annual crops, such as berry plants for example blackberries, blueberries, cranberries, raspberries and strawberries; cereals for example barley, maize (corn), millet, oats, rice, rye, sorghum triticale and wheat; fibre plants for example cotton, flax, hemp, jute and sisal; field crops for example sugar and fodder beet, coffee, hops, mustard, oilseed rape (canola), poppy, sugar cane, sunflower, tea and tobacco; fruit trees for example apple, apricot, avocado, banana, cherry, citrus, nectarine, peach, pear and plum; grasses for example Bermuda grass, bluegrass, bentgrass, centipede grass, fescue, ryegrass, St.
  • perennial and annual crops such as berry plants for example blackberries, blueberries, cranberries, raspberries and strawberries
  • cereals for example barley, maize (corn), millet, oats
  • Augustine grass and Zoysia grass herbs such as basil, borage, chives, coriander, lavender, lovage, mint, oregano, parsley, rosemary, sage and thyme; legumes for example beans, lentils, peas and soya beans; nuts for example almond, cashew, ground nut, hazelnut, peanut, pecan, pistachio and walnut; palms for example oil palm; ornamentals for example flowers, shrubs and trees; other trees, for example cacao, coconut, olive and rubber; vegetables for example asparagus, aubergine, broccoli, cabbage, carrot, cucumber, garlic, lettuce, marrow, melon, okra, onion, pepper, potato, pumpkin, rhubarb, spinach and tomato; and vines for example grapes.
  • herbs such as basil, borage, chives, coriander, lavender, lovage, mint, oregano, parsley, rosemary, sage and thyme
  • legumes for example beans, lentils, peas and soya beans
  • useful plants is to be understood as also including useful plants that have been rendered tolerant to herbicides like bromoxynil or classes of herbicides (such as, for example, HPPD inhibitors, ALS inhibitors, for example primisulfuron, prosulfuron and trifloxysulfuron, EPSPS (5-enol- pyrovyl-shikimate-3-phosphate-synthase) inhibitors, GS (glutamine synthetase) inhibitors or PPO (protoporphyrinogen-oxidase) inhibitors) as a result of conventional methods of breeding or genetic engineering.
  • herbicides like bromoxynil or classes of herbicides
  • EPSPS (5-enol- pyrovyl-shikimate-3-phosphate-synthase) inhibitors
  • GS glutamine synthetase
  • PPO protoporphyrinogen-oxidase
  • imazamox by conventional methods of breeding (mutagenesis) is Clearfield® summer rape (Canola).
  • crops that have been rendered tolerant to herbicides or classes of herbicides by genetic engineering methods include glyphosate- and glufosinate-resistant maize varieties commercially available under the trade names RoundupReady®, Herculex I® and LibertyLink®.
  • useful plants is to be understood as also including useful plants which have been so transformed by the use of recombinant DNA techniques that they are capable of synthesising one or more selectively acting toxins, such as are known, for example, from toxin-producing bacteria, especially those of the genus Bacillus.
  • YieldGard® (maize variety that expresses a CrylA(b) toxin); YieldGard Rootworm® (maize variety that expresses a CrylllB(bl ) toxin); YieldGard Plus® (maize variety that expresses a CrylA(b) and a CrylllB(bl ) toxin); Starlink® (maize variety that expresses a Cry9(c) toxin); Herculex I® (maize variety that expresses a CrylF(a2) toxin and the enzyme phosphinothricine N-acetyltransferase (PAT) to achieve tolerance to the herbicide glufosinate ammonium); NuCOTN 33B® (cotton variety that expresses a CrylA(c) toxin); Bollgard I® (cotton variety that expresses a CrylA(c) toxin); Bollgard II® (cotton variety that
  • crops is to be understood as including also crop plants which have been so transformed by the use of recombinant DNA techniques that they are capable of synthesising one or more selectively acting toxins, such as are known, for example, from toxin-producing bacteria, especially those of the genus Bacillus.
  • Toxins that can be expressed by such transgenic plants include, for example, insecticidal proteins from Bacillus cereus or Bacillus popilliae; or insecticidal proteins from Bacillus thuringiensis, such as ⁇ -endotoxins, e.g. CrylAb, CrylAc, Cryl F, Cry1 Fa2, Cry2Ab, Cry3A, Cry3Bb1 or Cry9C, or vegetative insecticidal proteins (Vip), e.g. Vip1 , Vip2, Vip3 or Vip3A; or insecticidal proteins of bacteria colonising nematodes, for example Photorhabdus spp.
  • insecticidal proteins from Bacillus cereus or Bacillus popilliae such as ⁇ -endotoxins, e.g. CrylAb, CrylAc, Cryl F, Cry1 Fa2, Cry2Ab, Cry3A, Cry3Bb1 or Cry9C, or vegetative insecticidal proteins
  • Xenorhabdus spp. such as Photorhabdus luminescens, Xenorhabdus nematophilus
  • toxins produced by animals such as scorpion toxins, arachnid toxins, wasp toxins and other insect-specific neurotoxins
  • toxins produced by fungi such as Streptomycetes toxins, plant lectins, such as pea lectins, barley lectins or snowdrop lectins
  • agglutinins proteinase inhibitors, such as trypsin inhibitors, serine protease inhibitors, patatin, cystatin, papain inhibitors
  • steroid metabolism enzymes such as 3-hydroxysteroidoxidase, ecdysteroid-UDP-glycosyl-transferase, cholesterol oxidases, ecd
  • ⁇ -endotoxins for example CrylAb, CrylAc, Cryl F, Cry1 Fa2, Cry2Ab, Cry3A, Cry3Bb1 or Cry9C, or vegetative insecticidal proteins (Vip), for example Vip1 , Vip2, Vip3 or Vip3A, expressly also hybrid toxins, truncated toxins and modified toxins.
  • Hybrid toxins are produced recombinantly by a new combination of different domains of those proteins (see, for example, WO 02/15701 ).
  • Truncated toxins for example a truncated CrylAb, are known.
  • modified toxins one or more amino acids of the naturally occurring toxin are replaced.
  • amino acid replacements preferably non-naturally present protease recognition sequences are inserted into the toxin, such as, for example, in the case of Cry3A055, a cathepsin-G-recognition sequence is inserted into a Cry3A toxin (see WO 03/018810).
  • Examples of such toxins or transgenic plants capable of synthesising such toxins are disclosed, for example, in EP-A-0 374 753, WO93/07278, W095/34656, EP-A-0 427 529, EP-A-451 878 and WO 03/052073.
  • Cryl-type deoxyribonucleic acids and their preparation are known, for example, from WO 95/34656, EP-A-0 367 474, EP-A-0 401 979 and WO 90/13651.
  • the toxin contained in the transgenic plants imparts to the plants tolerance to harmful insects.
  • insects can occur in any taxonomic group of insects, but are especially commonly found in the beetles (Coleoptera), two-winged insects (Diptera) and butterflies (Lepidoptera).
  • Transgenic plants containing one or more genes that code for an insecticidal resistance and express one or more toxins are known and some of them are commercially available. Examples of such plants are: YieldGard® (maize variety that expresses a CrylAb toxin); YieldGard Rootworm® (maize variety that expresses a Cry3Bb1 toxin); YieldGard Plus® (maize variety that expresses a CrylAb and a Cry3Bb1 toxin); Starlink® (maize variety that expresses a Cry9C toxin); Herculex I® (maize variety that expresses a Cry1 Fa2 toxin and the enzyme phosphinothricine N-acetyltransferase (PAT) to achieve tolerance to the herbicide glufosinate ammonium); NuCOTN 33B® (cotton variety that expresses a CrylAc toxin); Bollgard I® (cotton variety that expresses a
  • transgenic crops are:
  • Bt11 Maize from Syngenta Seeds SAS, Chemin de I'Hobit 27, F-31 790 St. Sauveur, France, registration number C/FR/96/05/10. Genetically modified Zea mays which has been rendered resistant to attack by the European corn borer (Ostrinia nubilalis and Sesamia nonagrioides) by transgenic expression of a truncated CrylAb toxin. Bt1 1 maize also transgenically expresses the enzyme PAT to achieve tolerance to the herbicide glufosinate ammonium. 2. Bt176 Maize from Syngenta Seeds SAS, Chemin de I'Hobit 27, F-31 790 St. Sauveur, France, registration number C/FR/96/05/10.
  • MIR604 Maize from Syngenta Seeds SAS, Chemin de I'Hobit 27, F-31 790 St. Sauveur, France, registration number C/FR/96/05/10. Maize which has been rendered insect-resistant by transgenic expression of a modified Cry3A toxin. This toxin is Cry3A055 modified by insertion of a cathepsin-G- protease recognition sequence. The preparation of such transgenic maize plants is described in WO 03/018810.
  • MON 863 Maize from Monsanto Europe S.A. 270-272 Avenue de Tervuren, B-1 150 Brussels, Belgium, registration number C/DE/02/9. MON 863 expresses a Cry3Bb1 toxin and has resistance to certain Coleoptera insects.
  • NK603 * MON 810 Maize from Monsanto Europe S.A. 270-272 Avenue de Tervuren, B-1 150 Brussels, Belgium, registration number C/GB/02/M3/03. Consists of conventionally bred hybrid maize varieties by crossing the genetically modified varieties NK603 and MON 810.
  • NK603 * MON 810 Maize transgenically expresses the protein CP4 EPSPS, obtained from Agrobacterium sp. strain CP4, which imparts tolerance to the herbicide Roundup® (contains glyphosate), and also a CrylAb toxin obtained from Bacillus thuringiensis subsp. kurstaki which brings about tolerance to certain Lepidoptera, include the European corn borer.
  • locus means fields in or on which plants are growing, or where seeds of cultivated plants are sown, or where seed will be placed into the soil. It includes soil, seeds, and seedlings, as well as established vegetation.
  • plants refers to all physical parts of a plant, including seeds, seedlings, saplings, roots, tubers, stems, stalks, foliage, and fruits.
  • plant propagation material is understood to denote generative parts of the plant, such as seeds, which can be used for the multiplication of the latter, and vegetative material, such as cuttings or tubers, for example potatoes.
  • vegetative material such as cuttings or tubers, for example potatoes.
  • seeds in the strict sense
  • roots in the strict sense
  • fruits in the tubers
  • bulbs rhizomes
  • parts of plants there can be mentioned for example seeds (in the strict sense), roots, fruits, tubers, bulbs, rhizomes and parts of plants.
  • Germinated plants and young plants which are to be transplanted after germination or after emergence from the soil may also be mentioned. These young plants can be protected before transplantation by a total or partial treatment by immersion.
  • plant propagation material is understood to denote seeds.
  • the compounds of Formula (IA) and (IB) may be used in unmodified form or, preferably, together with the adjuvants conventionally employed in the art of formulation. To this end they may be conveniently formulated in known manner to emulsifiable concentrates, coatable pastes, directly sprayable or dilutable solutions or suspensions, dilute emulsions, wettable powders, soluble powders, dusts, granulates, and also encapsulations e.g. in polymeric substances. As with the type of the compositions, the methods of application, such as spraying, atomising, dusting, scattering, coating or pouring, are chosen in accordance with the intended objectives and the prevailing circumstances. The compositions may also contain further adjuvants such as stabilizers, antifoams, viscosity regulators, binders or tackifiers as well as fertilizers, micronutrient donors or other formulations for obtaining special effects.
  • Suitable carriers and adjuvants can be solid or liquid and are substances useful in formulation technology, e.g. natural or regenerated mineral substances, solvents, dispersants, wetting agents, tackifiers, thickeners, binders or fertilizers.
  • Such carriers are for example described in WO 97/33890.
  • Suspension concentrates are aqueous formulations in which finely divided solid particles of the active compound are suspended. Such formulations include anti-settling agents and dispersing agents and may further include a wetting agent to enhance activity as well an anti-foam and a crystal growth inhibitor. In use, these concentrates are diluted in water and normally applied as a spray to the area to be treated. The amount of active ingredient may range from 0.5% to 95% of the concentrate.
  • Wettable powders are in the form of finely divided particles which disperse readily in water or other liquid carriers.
  • the particles contain the active ingredient retained in a solid matrix.
  • Typical solid matrices include fuller's earth, kaolin clays, silicas and other readily wet organic or inorganic solids. Wettable powders normally contain from 5% to 95% of the active ingredient plus a small amount of wetting, dispersing or emulsifying agent.
  • Emulsifiable concentrates are homogeneous liquid compositions dispersible in water or other liquid and may consist entirely of the active compound with a liquid or solid emulsifying agent, or may also contain a liquid carrier, such as xylene, heavy aromatic naphthas, isophorone and other non-volatile organic solvents. In use, these concentrates are dispersed in water or other liquid and normally applied as a spray to the area to be treated. The amount of active ingredient may range from 0.5% to 95% of the concentrate.
  • Granular formulations include both extrudates and relatively coarse particles and are usually applied without dilution to the area in which treatment is required.
  • Typical carriers for granular formulations include sand, fuller's earth, attapulgite clay, bentonite clays, montmorillonite clay, vermiculite, perlite, calcium carbonate, brick, pumice, pyrophyllite, kaolin, dolomite, plaster, wood flour, ground corn cobs, ground peanut hulls, sugars, sodium chloride, sodium sulphate, sodium silicate, sodium borate, magnesia, mica, iron oxide, zinc oxide, titanium oxide, antimony oxide, cryolite, gypsum, diatomaceous earth, calcium sulphate and other organic or inorganic materials which absorb or which can be coated with the active compound.
  • Granular formulations normally contain 5% to 25% of active ingredients which may include surface-active agents such as heavy aromatic naphthas, kerosene and other petroleum fractions, or vegetable oils
  • Dusts are free-flowing admixtures of the active ingredient with finely divided solids such as talc, clays, flours and other organic and inorganic solids which act as dispersants and carriers.
  • Microcapsules are typically droplets or granules of the active ingredient enclosed in an inert porous shell which allows escape of the enclosed material to the surroundings at controlled rates.
  • Encapsulated droplets are typically 1 to 50 microns in diameter.
  • the enclosed liquid typically constitutes 50 to 95% of the weight of the capsule and may include solvent in addition to the active compound.
  • Encapsulated granules are generally porous granules with porous membranes sealing the granule pore openings, retaining the active species in liquid form inside the granule pores.
  • Granules typically range from 1 millimetre to 1 centimetre and preferably 1 to 2 millimetres in diameter. Granules are formed by extrusion, agglomeration or prilling, or are naturally occurring.
  • Shell or membrane materials include natural and synthetic rubbers, cellulosic materials, styrene-butadiene copolymers, polyacrylonitriles, polyacrylates, polyesters, polyamides, polyureas, polyurethanes and starch xanthates.
  • compositions for agrochemical applications include simple solutions of the active ingredient in a solvent in which it is completely soluble at the desired concentration, such as acetone, alkylated naphthalenes, xylene and other organic solvents.
  • Pressurised sprayers wherein the active ingredient is dispersed in finely-divided form as a result of vaporisation of a low boiling dispersant solvent carrier, may also be used.
  • Suitable agricultural adjuvants and carriers that are useful in formulating the compositions of the invention in the formulation types described above are well known to those skilled in the art.
  • Liquid carriers that can be employed include, for example, water, toluene, xylene, petroleum naphtha, crop oil, acetone, methyl ethyl ketone, cyclohexanone, acetic anhydride, acetonitrile, acetophenone, amyl acetate, 2-butanone, chlorobenzene, cyclohexane, cyclohexanol, alkyl acetates, diacetonalcohol, 1 ,2-dichloropropane, diethanolamine, p-diethylbenzene, diethylene glycol, diethylene glycol abietate, diethylene glycol butyl ether, diethylene glycol ethyl ether, diethylene glycol methyl ether, ⁇ , ⁇ -dimethyl formamide, dimethyl sulfoxide, 1 ,4-dioxane, dipropylene glycol, dipropylene glycol methyl ether, dipropylene glyco
  • Suitable solid carriers include, for example, talc, titanium dioxide, pyrophyllite clay, silica, attapulgite clay, kieselguhr, chalk, diatomaxeous earth, lime, calcium carbonate, bentonite clay, fuller's earth, cotton seed hulls, wheat flour, soybean flour, pumice, wood flour, walnut shell flour and lignin.
  • a broad range of surface-active agents are advantageously employed in both said liquid and solid compositions, especially those designed to be diluted with carrier before application.
  • These agents when used, normally comprise from 0.1 % to 15% by weight of the formulation. They can be anionic, cationic, non-ionic or polymeric in character and can be employed as emulsifying agents, wetting agents, suspending agents or for other purposes.
  • Typical surface active agents include salts of alkyl sulfates, such as diethanolammonium lauryl sulphate; alkylarylsulfonate salts, such as calcium dodecylbenzenesulfonate; alkylphenol-alkylene oxide addition products, such as nonylphenol-C.sub.
  • alcohol-alkylene oxide addition products such as tridecyl alcohol-C.sub. 16 ethoxylate
  • soaps such as sodium stearate
  • alkylnaphthalenesulfonate salts such as sodium dibutylnaphthalenesulfonate
  • dialkyl esters of sulfosuccinate salts such as sodium di(2-ethylhexyl) sulfosuccinate
  • sorbitol esters such as sorbitol oleate
  • quaternary amines such as lauryl trimethylammonium chloride
  • polyethylene glycol esters of fatty acids such as polyethylene glycol stearate
  • salts of mono and dialkyl phosphate esters such as mono and dialkyl phosphate esters.
  • adjuvants commonly utilized in agricultural compositions include crystallisation inhibitors, viscosity modifiers, suspending agents, spray droplet modifiers, pigments, antioxidants, foaming agents, anti-foaming agents, light-blocking agents, compatibilizing agents, antifoam agents, sequestering agents, neutralising agents and buffers, corrosion inhibitors, dyes, odorants, spreading agents, penetration aids, micronutrients, emollients, lubricants and sticking agents.
  • biocidally active ingredients or compositions may be combined with the compositions of the invention and used in the methods of the invention and applied simultaneously or sequentially with the compositions of the invention. When applied simultaneously, these further active ingredients may be formulated together with the compositions of the invention or mixed in, for example, the spray tank. These further biocidally active ingredients may be fungicides, herbicides, insecticides, bactericides, acaricides, nematicides and/or plant growth regulators.
  • Pesticidal agents are referred to herein using their common name are known, for example, from “The Pesticide Manual”, 15th Ed., British Crop Protection Council 2009.
  • compositions of the invention may also be applied with one or more systemically acquired resistance inducers ("SAR" inducer).
  • SAR inducers are known and described in, for example, United States Patent No. US 6,919,298 and include, for example, salicylates and the commercial SAR inducer acibenzolar-S-methyl.
  • the compounds of Formula (IA) and (IB) are normally used in the form of agrochemical compositions and can be applied to the crop area or plant to be treated, simultaneously or in succession with further compounds.
  • These further compounds can be e.g. fertilizers or micronutrient donors or other preparations, which influence the growth of plants. They can also be selective herbicides or nonselective herbicides as well as insecticides, fungicides, bactericides, nematicides, molluscicides or mixtures of several of these preparations, if desired together with further carriers, surfactants or application promoting adjuvants customarily employed in the art of formulation.
  • the compounds of Formula (IA) and (IB) may be used in the form of (fungicidal) compositions for controlling or protecting against phytopathogenic microorganisms, comprising as active ingredient at least one compound of Formula (IA) or (IB) or of at least one preferred individual compound as defined herein, in free form or in agrochemically usable salt form, and at least one of the above-mentioned adjuvants.
  • the invention therefore provides a composition, preferably a fungicidal composition, comprising at least one compound of Formula (IA) or (IB), an agriculturally acceptable carrier and optionally an adjuvant.
  • An agricultural acceptable carrier is for example a carrier that is suitable for agricultural use.
  • Agricultural carriers are well known in the art.
  • said composition may comprise at least one or more pesticidally-active compounds, for example an additional fungicidal active ingredient in addition to the compound of Formula (IA) or (IB).
  • the compound of Formula (IA) or (IB) may be the sole active ingredient of a composition or it may be admixed with one or more additional active ingredients such as a pesticide, fungicide, synergist, herbicide or plant growth regulator where appropriate.
  • An additional active ingredient may, in some cases, result in unexpected synergistic activities.
  • Suitable additional active ingredients include the following: acycloamino acid fungicides, aliphatic nitrogen fungicides, amide fungicides, anilide fungicides, antibiotic fungicides, aromatic fungicides, arsenical fungicides, aryl phenyl ketone fungicides, benzamide fungicides, benzanilide fungicides, benzimidazole fungicides, benzothiazole fungicides, botanical fungicides, bridged diphenyl fungicides, carbamate fungicides, carbanilate fungicides, conazole fungicides, copper fungicides, dicarboximide fungicides, dinitrophenol fungicides, dithiocarbamate fungicides, dithiolane fungicides, furamide fungicides, furanilide fungicides, hydrazide fungicides, imidazole fungicides, mercury fungicides, morpholine fung
  • Suitable additional active ingredients also include the following: 3-difluoromethyl-
  • 1-methyl-1 H-pyrazole-4-carboxylic acid (9-dichloromethylene-1 ,2,3,4-tetrahydro-1 ,4-methano- naphthalen-5-yl)-amide, 3-difluoromethyl-1-methyl-1 H-pyrazole-4-carboxylic acid methoxy-[1-methyl-2- (2,4,6-trichlorophenyl)-ethyl]-amide, 1-methyl-3-difluoromethyl-1 H-pyrazole-4-carboxylic acid (2- dichloromethylene-3-ethyl-1-methyl-indan-4-yl)-amide (1072957-71-1 ), 1-methyl-3-difluoromethyl-1 H- pyrazole-4-carboxylic acid (4'-methylsulfanyl-biphenyl-2-yl)-amide, 1-methyl-3-difluoromethyl-4H- pyrazole-4-carboxylic acid [2-(2,4-dichloro-pheny
  • the compounds of the invention may also be used in combination with anthelmintic agents.
  • Such anthelmintic agents include, compounds selected from the macrocyclic lactone class of compounds such as ivermectin, avermectin, abamectin, emamectin, eprinomectin, doramectin, selamectin, moxidectin, nemadectin and milbemycin derivatives as described in EP- 357460, EP-
  • Additional anthelmintic agents include semisynthetic and biosynthetic avermectin/milbemycin derivatives such as those described in US-5015630, WO-9415944 and WO-
  • Additional anthelmintic agents include the benzimidazoles such as albendazole, cambendazole, fenbendazole, flubendazole, mebendazole, oxfendazole, oxibendazole, parbendazole, and other members of the class. Additional anthelmintic agents include imidazothiazoles and tetrahydropyrimidines such as tetramisole, levamisole, pyrantel pamoate, oxantel or morantel.
  • Additional anthelmintic agents include flukicides, such as triclabendazole and clorsulon and the cestocides, such as praziquantel and epsiprantel.
  • the compounds of the invention may be used in combination with derivatives and analogues of the paraherquamide/marcfortine class of anthelmintic agents, as well as the antiparasitic oxazolines such as those disclosed in US-5478855, US- 4639771 and DE-19520936.
  • the compounds of the invention may be used in combination with derivatives and analogues of the general class of dioxomorpholine antiparasitic agents as described in WO 96/15121 and also with anthelmintic active cyclic depsipeptides such as those described in WO 96/11945, WO 93/19053, WO
  • the compounds of the invention may be used in combination with other ectoparasiticides; for example, fipronil; pyrethroids; organophosphates; insect growth regulators such as lufenuron; ecdysone agonists such as tebufenozide and the like; neonicotinoids such as imidacloprid and the like.
  • ectoparasiticides for example, fipronil; pyrethroids; organophosphates; insect growth regulators such as lufenuron; ecdysone agonists such as tebufenozide and the like; neonicotinoids such as imidacloprid and the like.
  • the compounds of the invention may be used in combination with terpene alkaloids, for example those described in International Patent Application Publication Numbers WO 95/19363 or WO 04/72086, particularly the compounds disclosed therein.
  • Organophosphates acephate, azamethiphos, azinphos-ethyl, azinphos-methyl, bromophos, bromophos-ethyl, cadusafos, chlorethoxyphos, chlorpyrifos, chlorfenvinphos, chlormephos, demeton, demeton-S-methyl, demeton-S-methyl sulphone, dialifos, diazinon, dichlorvos, dicrotophos, dimethoate, disulfoton, ethion, ethoprophos, etrimfos, famphur, fenamiphos, fenitrothion, fensulfothion, fenthion, flupyrazofos, fonofos, formothion, fosthiazate, heptenophos, isazophos, isothioate, isoxathion, malathion, meth
  • Carbamates alanycarb, aldicarb, 2-sec-butylphenyl methylcarbamate, benfuracarb, carbaryl, carbofuran, carbosulfan, cloethocarb, ethiofencarb, fenoxycarb, fenthiocarb, furathiocarb, HCN-801 , isoprocarb, indoxacarb, methiocarb, methomyl, 5-methyl-m-cumenylbutyryl(methyl)carbamate, oxamyl, pirimicarb, propoxur, thiodicarb, thiofanox, triazamate, UC-51717.
  • Pyrethroids acrinathin, allethrin, alphametrin, 5-benzyl-3-furylmethyl (E)-(1 R)-cis-2,2-dimethyl- 3-(2-oxothiolan-3-ylidenemethyl)cyclopropanecarboxylate, bifenthrin, beta-cyfluthrin, cyfluthrin, a- cypermethrin, beta-cypermethrin, bioallethrin, bioallethrin((S)-cyclopentylisomer), bioresmethrin, bifenthrin, NCI-85193, cycloprothrin, cyhalothrin, cythithrin, cyphenothrin, deltamethrin, empenthrin, esfenvalerate, ethofenprox, fenfluthrin, fenpropathrin, fenvaler
  • Arthropod growth regulators a) chitin synthesis inhibitors: benzoylureas: chlorfluazuron, diflubenzuron, fluazuron, flucycloxuron, flufenoxuron, hexaflumuron, lufenuron, novaluron, teflubenzuron, triflumuron, buprofezin, diofenolan, hexythiazox, etoxazole, chlorfentazine; b) ecdysone antagonists: halofenozide, methoxyfenozide, tebufenozide; c) juvenoids: pyriproxyfen, methoprene (including S-methoprene), fenoxycarb; d) lipid biosynthesis inhibitors: spirodiclofen.
  • antiparasitics acequinocyl, amitraz, AKD-1022, ANS-1 18, azadirachtin, Bacillus thuringiensis, bensultap, bifenazate, binapacryl, bromopropylate, BTG-504, BTG-505, camphechlor, cartap, chlorobenzilate, chlordimeform, chlorfenapyr, chromafenozide, clothianidine, cyromazine, diacloden, diafenthiuron, DBI-3204, dinactin, dihydroxymethyldihydroxypyrrolidine, dinobuton, dinocap, endosulfan, ethiprole, ethofenprox, fenazaquin, flumite, MTI-800, fenpyroximate, fluacrypyrim, flubenzimine, flubrocythrinate, flufenzine, flufenprox, fluproxyfen, halofenprox, hydra
  • Biological agents Bacillus thuringiensis ssp aizawai, kurstaki, Bacillus thuringiensis delta endotoxin, baculovirus, entomopathogenic bacteria, virus and fungi.
  • Bactericides chlortetracycline, oxytetracycline, streptomycin.
  • TX means one compound selected from the group consisting of the compounds described in: Tables 1.1A to 1.25A or Table T1 (below); Tables 1.1 B to 1.10B Table T2 (below). an adjuvant selected from the group of substances consisting of petroleum oils (alternative name) (628) + TX,
  • an acaricide selected from the group of substances consisting of 1 ,1-bis(4-chlorophenyl)-2- ethoxyethanol (lUPAC name) (910) + TX, 2,4-dichlorophenyl benzenesulfonate (lUPAC/Chemical Abstracts name) (1059) + TX, 2-fluoro-A/-methyl-A/-1-naphthylacetamide (lUPAC name) (1295) + TX, 4- chlorophenyl phenyl sulfone (lUPAC name) (981 ) + TX, abamectin (1) + TX, acequinocyl (3) + TX, acetoprole [CCN] + TX, acrinathrin (9) + TX, aldicarb (16) + TX, aldoxycarb (863) + TX, alpha- cypermethrin (202) + TX, amidithion (870) + TX, amidoflu
  • an algicide selected from the group of substances consisting of bethoxazin [CCN] + TX, copper dioctanoate (lUPAC name) (170) + TX, copper sulfate (172) + TX, cybutryne [CCN] + TX, dichlone (1052) + TX, dichlorophen (232) + TX, endothal (295) + TX, fentin (347) + TX, hydrated lime [CCN] + TX, nabam (566) + TX, quinoclamine (714) + TX, quinonamid (1379) + TX, simazine (730) + TX, triphenyltin acetate (lUPAC name) (347) and triphenyltin hydroxide (lUPAC name) (347) + TX,
  • an anthelmintic selected from the group of substances consisting of abamectin (1 ) + TX, crufomate (101 1 ) + TX, doramectin (alternative name) [CCN] + TX, emamectin (291 ) + TX, emamectin benzoate (291 ) + TX, eprinomectin (alternative name) [CCN] + TX, ivermectin (alternative name) [CCN] + TX, milbemycin oxime (alternative name) [CCN] + TX, moxidectin (alternative name) [CCN] + TX, piperazine [CCN] + TX, selamectin (alternative name) [CCN] + TX, spinosad (737) and thiophanate (1435) + TX,
  • an avicide selected from the group of substances consisting of chloralose (127) + TX, endrin (1 122) + TX, fenthion (346) + TX, pyridin-4-amine (lUPAC name) (23) and strychnine (745) + TX, a bactericide selected from the group of substances consisting of 1 -hydroxy- 1 /- -pyridine-2- thione (lUPAC name) (1222) + TX, 4-(quinoxalin-2-ylamino)benzenesulfonamide (lUPAC name) (748) + TX, 8-hydroxyquinoline sulfate (446) + TX, bronopol (97) + TX, copper dioctanoate (lUPAC name) (170) + TX, copper hydroxide (lUPAC name) (169) + TX, cresol [CCN] + TX, dichlorophen (232) + TX, dipyrithione (1 105) + TX, dodicin (1 1
  • a soil sterilant selected from the group of substances consisting of iodomethane (lUPAC name) (542) and methyl bromide (537) + TX,
  • a chemosterilant selected from the group of substances consisting of apholate [CCN] + TX, bisazir (alternative name) [CCN] + TX, busulfan (alternative name) [CCN] + TX, diflubenzuron (250) + TX, dimatif (alternative name) [CCN] + TX, hemel [CCN] + TX, hempa [CCN] + TX, metepa [CCN] + TX, methiotepa [CCN] + TX, methyl apholate [CCN] + TX, morzid [CCN] + TX, penfluron (alternative name) [CCN] + TX, tepa [CCN] + TX, thiohempa (alternative name) [CCN] + TX, thiotepa (alternative name) [CCN] + TX, tretamine (alternative name) [CCN] and
  • an insect repellent selected from the group of substances consisting of 2-(octylthio)ethanol (lUPAC name) (591 ) + TX, butopyronoxyl (933) + TX, butoxy(polypropylene glycol) (936) + TX, dibutyl adipate (lUPAC name) (1046) + TX, dibutyl phthalate (1047) + TX, dibutyl succinate (lUPAC name) (1048) + TX, diethylamide [CCN] + TX, dimethyl carbate [CCN] + TX, dimethyl phthalate [CCN] + TX, ethyl hexanediol (1137) + TX, hexamide [CCN] + TX, methoquin-butyl (1276) + TX, methylneodecanamide [CCN] + TX, oxamate [CCN] and picaridin [CCN] + TX,
  • an insecticide selected from the group of substances consisting of 1-dichloro-1-nitroethane (lUPAC/Chemical Abstracts name) (1058) + TX, 1 ,1-dichloro-2,2-bis(4-ethylphenyl)ethane (lUPAC name) (1056), + TX, 1 ,2-dichloropropane (lUPAC/Chemical Abstracts name) (1062) + TX, 1 ,2- dichloropropane with 1 ,3-dichloropropene (lUPAC name) (1063) + TX, 1-bromo-2-chloroethane (lUPAC/Chemical Abstracts name) (916) + TX, 2,2,2-trichloro-1-(3,4-dichlorophenyl)ethyl acetate (lUPAC name) (1451 ) + TX, 2,2-dichlorovinyl 2-ethylsulfinylethyl methyl phosphate (lUPAC
  • a molluscicide selected from the group of substances consisting of bis(tributyltin) oxide (lUPAC name) (913) + TX, bromoacetamide [CCN] + TX, calcium arsenate [CCN] + TX, cloethocarb (999) + TX, copper acetoarsenite [CCN] + TX, copper sulfate (172) + TX, fentin (347) + TX, ferric phosphate (lUPAC name) (352) + TX, metaldehyde (518) + TX, methiocarb (530) + TX, niclosamide (576) + TX, niclosamide-olamine (576) + TX, pentachlorophenol (623) + TX, sodium pentachlorophenoxide (623) + TX, tazimcarb (1412) + TX, thiodicarb (799) + TX, tributyltin oxide (913)
  • a nematicide selected from the group of substances consisting of AKD-3088 (compound code)
  • a nitrification inhibitor selected from the group of substances consisting of potassium ethylxanthate [CCN] and nitrapyrin (580) + TX,
  • a plant activator selected from the group of substances consisting of acibenzolar (6) + TX, acibenzolar-S-methyl (6) + TX, probenazole (658) and Reynoutria sachalinensis extract (alternative name) (720) + TX,
  • a rodenticide selected from the group of substances consisting of 2-isovalerylindan-1 ,3-dione (lUPAC name) (1246) + TX, 4-(quinoxalin-2-ylamino)benzenesulfonamide (lUPAC name) (748) + TX, alpha-chlorohydrin [CCN] + TX, aluminium phosphide (640) + TX, antu (880) + TX, arsenous oxide (882) + TX, barium carbonate (891 ) + TX, bisthiosemi (912) + TX, brodifacoum (89) + TX, bromadiolone (91 ) + TX, bromethalin (92) + TX, calcium cyanide (444) + TX, chloralose (127) + TX, chlorophacinone (140) + TX, cholecalciferol (alternative name) (850) + TX, coumachlor (1004) + TX, co
  • a synergist selected from the group of substances consisting of 2-(2-butoxyethoxy)ethyl piperonylate (lUPAC name) (934) + TX, 5-(1 ,3-benzodioxol-5-yl)-3-hexylcyclohex-2-enone (lUPAC name) (903) + TX, farnesol with nerolidol (alternative name) (324) + TX, MB-599 (development code) (498) + TX, MGK 264 (development code) (296) + TX, piperonyl butoxide (649) + TX, piprotal (1343) + TX, propyl isomer (1358) + TX, S421 (development code) (724) + TX, sesamex (1393) + TX, sesasmolin (1394) and sulfoxide (1406) + TX,
  • an animal repellent selected from the group of substances consisting of anthraquinone (32) + TX, chloralose (127) + TX, copper naphthenate [CCN] + TX, copper oxychloride (171 ) + TX, diazinon (227) + TX, dicyclopentadiene (chemical name) (1069) + TX, guazatine (422) + TX, guazatine acetates (422) + TX, methiocarb (530) + TX, pyridin-4-amine (lUPAC name) (23) + TX, thiram (804) + TX, trimethacarb (840) + TX, zinc naphthenate [CCN] and ziram (856) + TX,
  • a virucide selected from the group of substances consisting of imanin (alternative name) [CCN] and ribavirin (alternative name) [CCN] + TX,
  • a wound protectant selected from the group of substances consisting of mercuric oxide (512) + TX, octhilinone (590) and thiophanate-methyl (802) + TX,
  • the active ingredient mixture of the compounds of Formula (IA) or (IB) selected from a compound 1.1 to 1.27 described in Table T1 (below), or a compound 2.1 to 2.26 described in Table T2 (below) and an active ingredient as described above are preferably in a mixing ratio of from 100: 1 to 1 :6000, especially from 50: 1 to 1 :50, more especially in a ratio of from 20: 1 to 1 :20, even more especially from 10:1 to 1 :10, very especially from 5:1 and 1 :5, special preference being given to a ratio of from 2:1 to 1 :2, and a ratio of from 4:1 to 2:1 being likewise preferred, above all in a ratio of 1 :1 , or 5:1 , or 5:2, or 5:3, or 5:4, or 4:1 , or 4:2, or 4:3, or 3:1 , or 3:2, or 2:1 , or 1 :5, or 2:5, or 3:5, or 4:5, or 1 :4, or 2:4, or 3:4, or 1 :3, or
  • the mixtures as described above can be used in a method for controlling pests, which comprises applying a composition comprising a mixture as described above to the pests or their environment, with the exception of a method for treatment of the human or animal body by surgery or therapy and diagnostic methods practised on the human or animal body.
  • the mixtures comprising a compound of Formula (IA) or (IB) selected from one of Tables 1.1 A to 1.25A, 1.1 B to 1.10B (below), or Table T1 or T2 (below), and one or more active ingredients as described above can be applied, for example, in a single "ready-mix” form, in a combined spray mixture composed from separate formulations of the single active ingredient components, such as a "tank-mix", and in a combined use of the single active ingredients when applied in a sequential manner, i.e. one after the other with a reasonably short period, such as a few hours or days.
  • compositions according to the invention can also comprise further solid or liquid auxiliaries, such as stabilizers, for example unepoxidized or epoxidized vegetable oils (for example epoxidized coconut oil, rapeseed oil or soya oil), antifoams, for example silicone oil, preservatives, viscosity regulators, binders and/or tackifiers, fertilizers or other active ingredients for achieving specific effects, for example bactericides, fungicides, nematocides, plant activators, molluscicides or herbicides.
  • auxiliaries such as stabilizers, for example unepoxidized or epoxidized vegetable oils (for example epoxidized coconut oil, rapeseed oil or soya oil), antifoams, for example silicone oil, preservatives, viscosity regulators, binders and/or tackifiers, fertilizers or other active ingredients for achieving specific effects, for example bactericides, fungicides, nematocides
  • compositions according to the invention are prepared in a manner known per se, in the absence of auxiliaries for example by grinding, screening and/or compressing a solid active ingredient and in the presence of at least one auxiliary for example by intimately mixing and/or grinding the active ingredient with the auxiliary (auxiliaries).
  • auxiliaries for example by grinding, screening and/or compressing a solid active ingredient and in the presence of at least one auxiliary for example by intimately mixing and/or grinding the active ingredient with the auxiliary (auxiliaries).
  • Another aspect of the invention is related to the use of a compound of Formula (IA) or (IB) or of a preferred individual compound as defined herein, of a composition comprising at least one compound of Formula (IA) or (IB) or at least one preferred individual compound as above-defined, or of a fungicidal or insecticidal mixture comprising at least one compound of Formula (IA) or (IB) or at least one preferred individual compound as above-defined, in admixture with other fungicides or insecticides as described above, for controlling or preventing infestation of plants, e.g. useful plants such as crop plants, propagation material thereof, e.g. seeds, harvested crops, e.g. harvested food crops, or non-living materials by insects or by phytopathogenic microorganisms, preferably fungal organisms.
  • useful plants such as crop plants, propagation material thereof, e.g. seeds, harvested crops, e.g. harvested food crops, or non-living materials by insects or by phytopathogenic microorganisms,
  • a further aspect of the invention is related to a method of controlling or preventing an infestation of plants, e.g., useful plants such as crop plants, propagation material thereof, e.g. seeds, harvested crops, e.g., harvested food crops, or of non-living materials by insects or by phytopathogenic or spoilage microorganisms or organisms potentially harmful to man, especially fungal organisms, which comprises the application of a compound of Formula (IA) or (IB) or of a preferred individual compound as above- defined as active ingredient to the plants, to parts of the plants or to the locus thereof, to the propagation material thereof, or to any part of the non-living materials.
  • useful plants such as crop plants, propagation material thereof, e.g. seeds, harvested crops, e.g., harvested food crops, or of non-living materials by insects or by phytopathogenic or spoilage microorganisms or organisms potentially harmful to man, especially fungal organisms
  • Controlling or preventing means reducing infestation by phytopathogenic or spoilage microorganisms or organisms potentially harmful to man, especially fungal organisms, to such a level that an improvement is demonstrated.
  • a preferred method of controlling or preventing an infestation of crop plants by phytopathogenic microorganisms, especially fungal organisms, or insects which comprises the application of a compound of Formula (IA) or (IB), or an agrochemical composition which contains at least one of said compounds, is foliar application.
  • the frequency of application and the rate of application will depend on the risk of infestation by the corresponding pathogen or insect.
  • the compounds of Formula (IA) and (IB) can also penetrate the plant through the roots via the soil (systemic action) by drenching the locus of the plant with a liquid formulation, or by applying the compounds in solid form to the soil, e.g. in granular form (soil application).
  • Such granulates can be applied to the flooded rice field.
  • the compounds of Formula (IA) and (IB) may also be applied to seeds (coating) by impregnating the seeds or tubers either with a liquid formulation of the fungicide or coating them with a solid formulation.
  • a formulation e.g. a composition containing the compound of Formula (IA) or (IB), and, if desired, a solid or liquid adjuvant or monomers for encapsulating the compound of Formula (IA) or (IB), may be prepared in a known manner, typically by intimately mixing and/or grinding the compound with extenders, for example solvents, solid carriers and, optionally, surface active compounds (surfactants).
  • extenders for example solvents, solid carriers and, optionally, surface active compounds (surfactants).
  • Advantageous rates of application are normally from 5g to 2kg of active ingredient (a.i.) per hectare (ha), preferably from 10g to 1 kg a.i./ha, most preferably from 20g to 600g a.i./ha.
  • convenient dosages are from 10mg to 1g of active substance per kg of seeds.
  • rates of 0.001 to 50g of a compound of Formula (IA) or (IB) per kg of seed preferably from 0.01 to 10g per kg of seed are generally sufficient.
  • composition comprising a compound of Formula (IA) or (IB) according to the present invention is applied either preventative, meaning prior to disease development or curative, meaning after disease development.
  • compositions of the invention may be employed in any conventional form, for example in the form of a twin pack, a powder for dry seed treatment (DS), an emulsion for seed treatment (ES), a flowable concentrate for seed treatment (FS), a solution for seed treatment (LS), a water dispersible powder for seed treatment (WS), a capsule suspension for seed treatment (CF), a gel for seed treatment (GF), an emulsion concentrate (EC), a suspension concentrate (SC), a suspo-emulsion (SE), a capsule suspension (CS), a water dispersible granule (WG), an emulsifiable granule (EG), an emulsion, water in oil (EO), an emulsion, oil in water (EW), a micro-emulsion (ME), an oil dispersion (OD), an oil miscible flowable (OF), an oil miscible liquid (OL), a soluble concentrate (SL), an ultra-low volume suspension (SU), an ultra-low volume liquid (UL), a technical concentrate (TK
  • compositions may be produced in conventional manner, e.g. by mixing the active ingredients with appropriate formulation inerts (diluents, solvents, fillers and optionally other formulating ingredients such as surfactants, biocides, anti-freeze, stickers, thickeners and compounds that provide adjuvancy effects).
  • appropriate formulation inerts diiluents, solvents, fillers and optionally other formulating ingredients such as surfactants, biocides, anti-freeze, stickers, thickeners and compounds that provide adjuvancy effects.
  • conventional slow release formulations may be employed where long lasting efficacy is intended.
  • Particularly formulations to be applied in spraying forms such as water dispersible concentrates (e.g. EC, SC, DC, OD, SE, EW, EO and the like), wettable powders and granules, may contain surfactants such as wetting and dispersing agents and other compounds that provide adjuvancy effects, e.g.
  • a seed dressing formulation is applied in a manner known per se to the seeds employing the combination of the invention and a diluent in suitable seed dressing formulation form, e.g. as an aqueous suspension or in a dry powder form having good adherence to the seeds.
  • suitable seed dressing formulation form e.g. as an aqueous suspension or in a dry powder form having good adherence to the seeds.
  • seed dressing formulations are known in the art.
  • Seed dressing formulations may contain the single active ingredients or the combination of active ingredients in encapsulated form, e.g. as slow release capsules or microcapsules.
  • the formulations include from 0.01 to 90% by weight of active agent, from 0 to 20% agriculturally acceptable surfactant and 10 to 99.99% solid or liquid formulation inerts and adjuvant(s), the active agent consisting of at least the compound of Formula (IA) or (IB) optionally together with other active agents, particularly microbiocides or conservatives or the like.
  • Concentrated forms of compositions generally contain in between about 2 and 80%, preferably between about 5 and 70% by weight of active agent.
  • Application forms of formulation may for example contain from 0.01 to 20% by weight, preferably from 0.01 to 5% by weight of active agent. Whereas commercial products will preferably be formulated as concentrates, the end user will normally employ diluted formulations.
  • Table 1.1 A This table discloses 25 specific compounds of the formula (T-1 A):
  • Table 1A wherein n is 0, A 1 is C-R 1 , A 2 is C-R 2 , and R 2 , R 3 , R 4 , and R 8 are hydrogen, R is fluorine, and R 7 is as defined below in the Table 1A.
  • Tables 1.2A to 1.25A make available 25 individual compounds of the formula (T-1A) in which n, A 1 , A 2 , R 1 , R 2 , R 3 , R 4 , R 5 , R 6 , and R 8 are as specifically defined in Tables 1.2A to 1.25A, which refer to Table 1 A wherein R 7 is specifically defined.
  • Table 1A
  • Table 1 ,2A This table discloses 25 specific compounds of formula (T-1 A) wherein n is 0, A 1 is C-R ⁇ A 2 is C-R 2 , and R 2 , R 3 , and R 4 are hydrogen, R is fluorine, R 8 is methyl, and R 7 is as defined above in the Table 1A.
  • Table 1.3A This table discloses 25 specific compounds of formula (T-1 A) wherein n is 0, A 1 is C-R 1 , A 2 is C-R 2 , and R 2 , R 3 , and R 4 are hydrogen, R is fluorine, R 8 is allyl, and R 7 is as defined above in the Table 1A.
  • Table 1 ,4A This table discloses 25 specific compounds of formula (T-1 A) wherein n is 0, A 1 is C-R 1 , A 2 is C-R 2 , and R 2 , R 3 , and R 4 are hydrogen, R is fluorine, R 8 is propargyl, and R 7 is as defined above in the Table 1A.
  • Table 1.5A This table discloses 25 specific compounds of formula (T-1 A) wherein n is 0, A 1 is C-R 1 , A 2 is C-R 2 , and R 2 , R 3 , and R 4 are hydrogen, R is fluorine, R 8 is benzyl, and R 7 is as defined above in the Table 1A.
  • Table 1.6A This table discloses 25 specific compounds of formula (T-1 A) wherein n is 0, A 1 is C-R 1 , A 2 is C-R 2 , and R , R 2 , R 4 , and R 8 are hydrogen, R 3 is fluorine, and R 7 is as defined above in the Table 1A.
  • Table 1.7A This table discloses 25 specific compounds of formula (T-1A) wherein n is 0, A 1 is C-R 1 , A 2 is C-R 2 , and R , R 2 , and R 4 are hydrogen, R 3 is fluorine, R 8 is methyl, and R 7 is as defined above in the Table 1A.
  • Table 1.8A This table discloses 25 specific compounds of formula (T-1A) wherein n is 0, A 1 is C-R 1 , A 2 is C-R 2 , and R , R 2 , and R 4 are hydrogen, R 3 is fluorine, R 8 is allyl, and R 7 is as defined above in the Table 1A.
  • Table 1.9A This table discloses 25 specific compounds of formula (T-1A) wherein n is 0, A 1 is C-R 1 , A 2 is C-R 2 , and R , R 2 , and R 4 are hydrogen, R 3 is fluorine, R 8 is propargyl, and R 7 is as defined above in the Table 1A.
  • Table 1.10A This table discloses 25 specific compounds of formula (T-1A) wherein n is 0, A 1 is C-R 1 , A 2 is C-R 2 , and R , R 2 , and R 4 are hydrogen, R 3 is fluorine, R 8 is benzyl, and R 7 is as defined above in the Table 1 A.
  • Table 1.11 A This table discloses 25 specific compounds of formula (T-1A) wherein n is 0, A 1 is C-R 1 , A 2 is C-R 2 , and R 3 , R 4 , and R 8 are hydrogen, R and R 2 are fluorine, and R 7 is as defined above in the Table 1A.
  • Table 1.12A This table discloses 25 specific compounds of formula (T-1A) wherein n is 0, A 1 is C-R 1 , A 2 is C-R 2 , and R 3 and R 4 are hydrogen, R and R 2 are fluorine, R 8 is methyl, and R 7 is as defined above in the Table 1A.
  • Table 1.13A This table discloses 25 specific compounds of formula (T-1A) wherein n is 0, A 1 is C-R 1 , A 2 is C-R 2 , and R 3 and R 4 are hydrogen, R and R 2 are fluorine, R 8 is allyl, and R 7 is as defined above in the Table 1A.
  • Table 1.14A This table discloses 25 specific compounds of formula (T-1A) wherein n is 0, A 1 is C-R 1 , A 2 is C-R 2 , and R 3 and R 4 are hydrogen, R and R 2 are fluorine, R 8 is propargyl, and R 7 is as defined above in the Table 1A.
  • Table 1.15A This table discloses 25 specific compounds of formula (T-1A) wherein n is 0, A 1 is C-R 1 , A 2 is C-R 2 , and R 3 and R 4 are hydrogen, R and R 2 are fluorine, R 8 is benzyl, and R 7 is as defined above in the Table 1A.
  • Table 1.16A This table discloses 25 specific compounds of formula (T-1A) wherein n is 0, A 1 is N, A 2 is C-R 2 , and R 2 , R 3 , R 4 , and R 8 are hydrogen, and R 7 is as defined above in the Table 1A.
  • Table 1.17A This table discloses 25 specific compounds of formula (T-1A) wherein n is 0, A 1 is N, A 2 is C-R 2 , and R 2 , R 3 , and R 4 are hydrogen, R 8 is methyl, and R 7 is as defined above in the Table 1A.
  • Table 1.18A This table discloses 25 specific compounds of formula (T-1A) wherein n is 0, A 1 is N, A 2 is C-R 2 , and R 2 , R 3 , and R 4 are hydrogen, R 8 is allyl, and R 7 is as defined above in the Table 1A.
  • Table 1.19A This table discloses 25 specific compounds of formula (T-1A) wherein n is 0, A 1 is N, A 2 is C-R 2 , and R 2 , R 3 , and R 4 are hydrogen, R 8 is propargyl, and R 7 is as defined above in the Table 1A.
  • Table 1 ,20A This table discloses 25 specific compounds of formula (T-1A) wherein n is 0, A 1 is N, A 2 is C-R 2 , and R 2 , R 3 , and R 4 are hydrogen, R 8 is benzyl, and R 7 is as defined above in the Table 1A.
  • Table 1.21 A This table discloses 25 specific compounds of formula (T-1A) wherein n is 1 , A 1 is C-R 1 , A 2 is C-R 2 , and R , R 2 , R 4 , and R 8 are hydrogen, R 3 is fluorine, and R 7 is as defined above in the Table 1A.
  • Table 1.22A This table discloses 25 specific compounds of formula (T-1A) wherein n is 1 , A 1 is C-R 1 , A 2 is C-R 2 , and R , R 2 , and R 4 are hydrogen, R 3 is fluorine, R 8 is methyl, and R 7 is as defined above in the Table 1A.
  • Table 1.23A This table discloses 25 specific compounds of formula (T-1A) wherein n is 1 , A 1 is C-R 1 , A 2 is C-R 2 , and R , R 2 , and R 4 are hydrogen, R 3 is fluorine, R 8 is allyl, and R 7 is as defined above in the Table 1A.
  • Table 1.24A This table discloses 25 specific compounds of formula (T-1A) wherein n is 1 , A 1 is C-R 1 , A 2 is C-R 2 , and R , R 2 , and R 4 are hydrogen, R 3 is fluorine, R 8 is propargyl, and R 7 is as defined above in the Table 1A.
  • Table 1.25A This table discloses 25 specific compounds of formula (T-1A) wherein n is 1 , A 1 is C-R 1 , A 2 is C-R 2 , and R , R 2 , and R 4 are hydrogen, R 3 is fluorine, R 8 is benzyl, and R 7 is as defined above in the Table 1A.
  • Table 1.1B This table discloses 25 specific compounds of the formula (T-1 B):
  • Table 1.2B This table discloses 25 specific compounds of formula (T-1 B) wherein n is 0, A 1 is C-R 1 , A 2 is C-R 2 , and R , R 2 , R 3 , and R 4 are hydrogen, R 8 is methyl, and R 7 is as defined above in the Table 1 B.
  • Table 1.3B This table discloses 25 specific compounds of formula (T-1 B) wherein n is 0, A 1 is C-R , A 2 is C-R 2 , and R , R 2 , R 3 , and R 4 are hydrogen, R 8 is allyl, and R 7 is as defined above in the Table 1 B.
  • Table 1.4B This table discloses 25 specific compounds of formula (T-1 B) wherein n is 0, A 1 is C-R 1 , A 2 is C-R 2 , and R , R 2 , R 3 , and R 4 are hydrogen, R 8 is propargyl, and R 7 is as defined above in the Table 1 B.
  • Table 1.5B This table discloses 25 specific compounds of formula (T-1 B) wherein n is 0, A 1 is C-R 1 , A 2 is C-R 2 , and R , R 2 , R 3 , and R 4 are hydrogen, R 8 is benzyl, and R 7 is as defined above in the Table 1 B.
  • Table 1.6B This table discloses 25 specific compounds of formula (T-1 B) wherein n is 1 , A 1 is C-R 1 , A 2 is C-R 2 , and R , R 2 , R 3 , R 4 , R 5 , R 6 , and R 8 are hydrogen, and R 7 is as defined above in the Table 1 B.
  • Table 1.7B This table discloses 25 specific compounds of formula (T-1 B) wherein n is 1 , A 1 is C-R , A 2 is C-R 2 , and R , R 2 , R 3 , R 4 , R 5 , and R 6 are hydrogen, R 8 is methyl, and R 7 is as defined above in the Table 1 B.
  • Table 1.8B This table discloses 25 specific compounds of formula (T-1 B) wherein n is 1 , A 1 is C-R , A 2 is C-R 2 , and R , R 2 , R 3 , R 4 , R 5 , and R 6 are hydrogen, R 8 is allyl, and R 7 is as defined above in the Table 1 B.
  • Table 1.9B This table discloses 25 specific compounds of formula (T-1 B) wherein n is 1 , A 1 is C-R , A 2 is C-R 2 , and R , R 2 , R 3 , R 4 , R 5 , and R 6 are hydrogen, R 8 is propargyl, and R 7 is as defined above in the Table 1 B.
  • Table 1.1 OB This table discloses 25 specific compounds of formula (T-1 B) wherein n is 1 , A 1 is C-R 1 , A 2 is C-R 2 , and R , R 2 , R 3 , R 4 , R 5 , and R 6 are hydrogen, R 8 is benzyl, and R 7 is as defined above in the Table 1 B.
  • the compounds of the invention can be distinguished from known compounds by virtue of greater efficacy at low application rates, which can be verified by the person skilled in the art using the experimental procedures outlined in the Examples, using lower application rates if necessary, for example 50 ppm, 12.5 ppm, 6 ppm, 3 ppm, 1.5 ppm, 0.8 ppm or 0.2 ppm.
  • Compounds of Formula (I) may possess any number of benefits including, inter alia, advantageous levels of biological activity for protecting plants against diseases that are caused by fungi or superior properties for use as agrochemical active ingredients (for example, greater biological activity, an advantageous spectrum of activity, an increased safety profile (including improved crop tolerance), improved physico-chemical properties, or increased biodegradability).
  • LC/MS means Liquid Chromatography Mass Spectrometry and the description of the apparatus and the method (Methods A, B and C) is as follows:
  • Type of column Waters ACQUITY UPLC HSS T3; Column length: 30 mm; Internal diameter of column: 2.1 mm; Particle Size: 1 .8 micron; Temperature: 60°C.
  • the description of the LC/MS apparatus and the method C is:
  • Type of column Waters ACQUITY UPLC BEH C18; Column length: 50 mm; Internal diameter of column: 2.1 mm; Particle Size: 1 .7 micron; Temperature: 35°C.
  • enantiomerically pure final compounds may be obtained from racemic materials as appropriate via standard physical separation techniques, such as reverse phase chiral chromatography, or through stereoselective synthetic techniques, e.g., by using chiral starting materials.
  • the active ingredient is thoroughly mixed with the adjuvants and the mixture is thoroughly ground in a suitable mill, affording wettable powders that can be diluted with water to give suspensions of the desired concentration.
  • the active ingredient is thoroughly mixed with the adjuvants and the mixture is thoroughly ground in a suitable mill, affording powders that can be used directly for seed treatment.
  • Emulsions of any required dilution which can be used in plant protection, can be obtained from this concentrate by dilution with water.
  • Ready-for-use dusts are obtained by mixing the active ingredient with the carrier and grinding the mixture in a suitable mill. Such powders can also be used for dry dressings for seed.
  • the active ingredient is mixed and ground with the adjuvants, and the mixture is moistened with water.
  • the mixture is extruded and then dried in a stream of air.
  • the finely ground active ingredient is uniformly applied, in a mixer, to the kaolin moistened with polyethylene glycol. Non-dusty coated granules are obtained in this manner.
  • the finely ground active ingredient is intimately mixed with the adjuvants, giving a suspension concentrate from which suspensions of any desired dilution can be obtained by dilution with water.
  • a suspension concentrate from which suspensions of any desired dilution can be obtained by dilution with water.
  • living plants as well as plant propagation material can be treated and protected against infestation by microorganisms, by spraying, pouring or immersion.
  • the finely ground active ingredient is intimately mixed with the adjuvants, giving a flowable concentrate from which suspensions of any desired dilution can be obtained by dilution with water.
  • dilutions living plants as well as plant propagation material can be treated and protected against infestation by microorganisms, by spraying, pouring or immersion.
  • the obtained capsule suspension is stabilized by adding 0.25 parts of a thickener and 3 parts of a dispersing agent.
  • the capsule suspension formulation contains 28% of the active ingredients.
  • the medium capsule diameter is 8-15 microns.
  • the resulting formulation is applied to seeds as an aqueous suspension in an apparatus suitable for that purpose.
  • NBS /V-bromosuccinimide
  • LC/MS Liquid Chromatography Mass Spectrometry (description of the apparatus and the methods used for LC/MS analysis are given above)
  • Example 1 This example illustrates the preparation 2-fluoro-N-methoxy-4-[5-(trifluoromethyl)-1 ,2,4- oxadiazol-3-yl]benzamide (Com ound 1 .1 of Table T1 )
  • Step 1 Preparation of 2-fluoro-4-(N-hydroxycarbamimidoyl)-benzoic acid
  • Step 2 Preparation of 2-fluoro-4- 5-(trifluoromethyl)-1 ,2,4-oxadiazol-3-yl)benzoic acid
  • Trifluoroacetic anhydride (4.1 mL) was added dropwise to a stirred suspension of 2-fluoro-4-(N- hydroxycarbamimidoyl)-benzoic acid (3.80 g, 19.0 mmol) in THF (77 mL) at 10 to 15 °C. The beige suspension was warmed to room temperature and stirred overnight. After evaporation, the crude product was stirred with heptane/ethylacetate (95:5), filtered and dried under reduced pressure at 50 °C to yield 2-fluoro-4-(5-(trifluoromethyl)-1 ,2,4-oxadiazol-3-yl)benzoic acid as yellow solid, mp: 175-177 °C.
  • 1 H NMR 400 MHz, DMSO-d 6 ) ⁇ ppm: 13.55 (s, 1 H), 8.12 (t, 1 H), 8.00 (d, 1 H), 7.94 (d, 1 H).
  • Step 3 Preparation of 2-fluoro-4- 5-(trifluoromethyl)-[1 ,2,4]oxadiazol-3-yl)-benzoyl chloride
  • Example 2 This example illustrates the preparation of N-(cyclopropylmethyl)-2-fluoro-N-methoxy-4-[5- (trifluoromethyl)-1 ,2,4-oxadiazol-3-yl]benzamide (Compound 1.8 of Table T1 )
  • Step 2 Preparation of 3-(p-tolyl)-5-(trifluoromethyl)-1 ,2,4-oxadiazole
  • Step 3a Preparation of 3-[4-(bromomethyl)phenyll-5-(trifluoromethyl)-1 ,2,4-oxadiazole
  • Step 3b Preparation of 3-[4-(bromomethyl)phenyll-5-(trifluoromethyl)-1 ,2,4-oxadiazole
  • Step 4 Preparation of 2-[4-[5-(trifluoromethyl)-1 ,2,4-oxadiazol-3-yllphenyllacetonitrile
  • Step 7 Preparation of N-allyloxy-2-[4-[5-(trifluoromethyl)-1 ,2,4-oxadiazol-3-yllphenyllacetamide
  • Leaf disks or leaf segments of various plant species are cut from plants grown in a greenhouse.
  • the cut leaf disks or segments are placed in multiwell plates (24-well format) onto water agar.
  • the leaf disks are sprayed with a test solution before (preventative) or after (curative) inoculation.
  • Compounds to be tested are prepared as DMSO solutions (max. 10 mg/ml) which are diluted to the appropriate concentration with 0.025% Tween20 just before spraying.
  • the inoculated leaf disks or segments are incubated under defined conditions (temperature, relative humidity, light, etc.) according to the respective test system.
  • a single evaluation of disease level is carried out 3 to 14 days after inoculation, depending on the pathosystem. Percent disease control relative to the untreated check leaf disks or segments is then calculated.
  • Mycelia fragments or conidia suspensions of a fungus prepared either freshly from liquid cultures of the fungus or from cryogenic storage, are directly mixed into nutrient broth.
  • DMSO solutions of the test compound (max. 10 mg/ml) are diluted with 0.025% Tween20 by a factor of 50 and 10 ⁇ of this solution is pipetted into a microtiter plate (96-well format).
  • the nutrient broth containing the fungal spores/mycelia fragments is then added to give an end concentration of the tested compound.
  • the test plates are incubated in the dark at 24°C and 96% relative humidity. The inhibition of fungal growth is determined photometrically after 2 to 7 days, depending on the pathosystem, and percent antifungal activity relative to the untreated check is calculated.
  • Example 1 Fungicidal activity against Puccinia recondita f. sp. tritici I wheat / leaf disc preventative (Brown rust)
  • Wheat leaf segments cv. Kanzler are placed on agar in multiwell plates (24-well format) and sprayed with the formulated test compound diluted in water.
  • the leaf disks are inoculated with a spore suspension of the fungus 1 day after application.
  • the inoculated leaf segments are incubated at 19 °C and 75% rh under a light regime of 12 h light / 12 h darkness in a climate cabinet and the activity of a compound is assessed as percent disease control compared to untreated when an appropriate level of disease damage appears in untreated check leaf segments (7 - 9 days after application).
  • Example 2 Fungicidal activity against Puccinia recondita f. sp. tritici I wheat / leaf disc curative (Brown rust)
  • Wheat leaf segments cv. Kanzler are placed on agar in multiwell plates (24-well format). The leaf segments are inoculated with a spore suspension of the fungus. Plates are stored in darkness at 19 °C and 75% rh. The formulated test compound diluted in water is applied 1 day after inoculation. The leaf segments are incubated at 19 °C and 75% rh under a light regime of 12 h light / 12 h darkness in a climate cabinet and the activity of a compound is assessed as percent disease control compared to untreated when an appropriate level of disease damage appears in untreated check leaf segments (6 - 8 days after application).
  • Example 3 Fungicidal activity against Phakopsora pachyrhizi I soybean / leaf disc preventative (Asian soybean rust) Soybean leaf disks are placed on water agar in multiwell plates (24-well format) and sprayed with the formulated test compound diluted in water. One day after application leaf discs are inoculated by spraying a spore suspension on the lower leaf surface. After an incubation period in a climate cabinet of 24-36 hours in darkness at 20 °C and 75% rh leaf disc are kept at 20 °C with 12 h light / 12 h darkness and 75% rh. The activity of a compound is assessed as percent disease control compared to untreated when an appropriate level of disease damage appears in untreated check leaf disks (12 - 14 days after application).
  • Example 4 fungicidal activity against Glomerella lagenarium (Colletotrichum lagenarium) liguid culture / cucumber / preventative (Anthracnose)
  • Conidia of the fungus from cryogenic storage are directly mixed into nutrient broth (PDB potato dextrose broth). After placing a (DMSO) solution of test compound into a microtiter plate (96-well format), the nutrient broth containing the fungal spores is added. The test plates are incubated at 24 °C and the inhibition of growth is measured photometrically 3-4 days after application.
  • nutrient broth PDB potato dextrose broth
  • Field bean leaf discs are placed on water agar in multiwell plates (96-well format) and 10 ⁇ of the formulated test compound diluted in acetone and a spreader pipetted onto the leaf disc. Two hours after application leaf discs are inoculated by spraying a spore suspension on the lower leaf surface. The leaf discs are incubated in a climate cabinet at 22°C with 18 hour day and 70% relative humidity. The activity of a compound is assessed as percent disease control compared to untreated when an appropriate level of disease damage appears in untreated check leaf disks (12 days after application).
  • the following compounds at 100 ppm in the applied formulation give at least 80% disease control in this test when compared to untreated control leaf discs under the same conditions, which show extensive disease development.

Abstract

L'invention concerne des composés représentés par la formule (IA) ou la formula (IB): (IA/IB), dans laquelle les substituants sont tels que définis dans la revendication 1. Ces composés sont utiles en tant que pesticides, et en particulier en tant que fongicides.
EP17726886.9A 2016-05-20 2017-05-19 Dérivés d'oxadiazole microbiocides Withdrawn EP3458446A1 (fr)

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PCT/EP2017/062173 WO2017198852A1 (fr) 2016-05-20 2017-05-19 Dérivés d'oxadiazole microbiocides

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US11286242B2 (en) 2018-01-30 2022-03-29 Pi Industries Ltd. Oxadiazoles for use in controlling phytopathogenic fungi
EP3762367A1 (fr) 2018-03-09 2021-01-13 PI Industries Ltd. Composés hétérocycliques en tant que fongicides
AR116558A1 (es) 2018-10-01 2021-05-19 Pi Industries Ltd Oxadiazoles
WO2020070611A1 (fr) 2018-10-01 2020-04-09 Pi Industries Ltd Oxadiazoles utilisés comme fongicides
WO2020208509A1 (fr) 2019-04-08 2020-10-15 Pi Industries Limited Nouveaux composés d'oxadiazole pour la lutte ou la prévention contre des champignons phytopathogènes
EP3953353A1 (fr) 2019-04-08 2022-02-16 PI Industries Ltd. Nouveaux composés d'oxadiazole pour la lutte contre ou la prévention contre des champignons phytopathogènes
WO2021219418A1 (fr) 2020-04-29 2021-11-04 Basf Se Préparation de carboxyamides aromatiques par réaction de carbonylation catalysée au palladium
EP4143159B1 (fr) 2020-04-29 2024-04-10 Basf Se Préparation de carboxamides aromatiques à partir d'une réaction de carbonylation catalysée au palladium
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JP2019521094A (ja) 2019-07-25
US20200138027A1 (en) 2020-05-07
WO2017198852A1 (fr) 2017-11-23
CN109153657A (zh) 2019-01-04
US11154060B2 (en) 2021-10-26

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